α-arylacrylates and fungicides containing these compounds

ABSTRACT

α-Arylacrylates of the general formula I ##STR1## where Y is substituted or unsubstituted, alkenylene, alkynylene, O,S(O) m , N, oxycarbonyl, carbonyloxy, oxycarbonylalkylene, carbonyloxyalkylene, oxyalkyleneoxy, oxyalkylene, alkyleneoxy, thioalkylene, azo, carbonylamino, aminocarbonyl or aminocarbonyloxy, and 
     Z is hydrogen, halogen, alkyl, alkenyl, cycloalkyl, alkynyl, aryl, arylalkyl, arylalkenyl, aryloxy, aryloxyalkyl, alkoxyalkyl, haloalkyl, aryloxyalkoxy, alkoxycarbonyl, which are substituted or unsubstituted, or is a 5-membered heterocyclic structure in which two adjacent substituents may form an aromatic or heteroaromatic ring, 
     and fungicides containing these compounds.

The present invention relates to novel α-arylacrylates, their preparation and their use as fungicides.

Methyl α-phenylacrylate is known (C.A. Reg. No. 1865-29-8).

We have found that novel α-arylacrylate derivatives of the formula I ##STR2## where Y is unsubstituted or substituted C₁ -C₄ -alkylene, unsubstituted or substituted C₂ -C₄ -alkenylene, C₂ -C₄ -alkynylene, O,S(O)_(m) (m=0, 1 or 2), unsubstituted or C₁ -C₄ -alkyl-substituted N, oxycarbonyl, carbonyloxy, C₁ -C₁₀ -oxycarbonylalkylene, C₁ -C₁₀ -carbonyloxyalkylene, C₂ -C₁₀ -oxyalkyleneoxy, C₁ -C₁₀ -oxyalkylene, C₁ -C₁₀ -alkyleneoxy, C₁ -C₁₀ -thioalkylene, azo, unsubstituted or C₁ -C₄ -alkyl-substituted carbonylamino, unsubstituted or C₁ -C₄ -alkyl-substituted aminocarbonyl or unsubstituted or C₁ -C₄ -alkyl-substituted aminocarbonyloxy and

Z is hydrogen, halogen, C₁ -C₁₈ -alkyl, C₂ -C₁₈ -alkenyl, C₃ -C₈ -cycloalkyl, C₂ -C₄ -alkynyl, aryl, aryl-C₁ -C₁₀ -alkyl, aryl-C₂ -C₁₀ -alkenyl, aryloxy, aryloxy-C₁ -C₁₀ -alkyl, alkoxy-C₁ -C₁₀ -alkyl, halo-C₁ -C₁₀ -alkyl, aryloxy-C₁ -C₄ -alkoxy, C₁ -C₄ -alkoxycarbonyl, which are unsubstituted or substituted by halogen, cyano, nitro, C₁ -C₄ -alkyl, C₂ -C₄ -alkenyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, C₂ -C₄ -haloalkenyl, C₁ -C₄ -alkoxycarbonyl, unsubstituted or substituted phenyl or unsubstituted or substituted phenoxy, or is C-bonded, unsubstituted or substituted 5-membered heterocyclic structure which contains one to four indentical or different heteroatoms, i.e. nitrogen, oxygen or sulfur in that two adjacent substituents may form an aromatic or heteroaromatic ring which may be bonded to an ethylene unit, have a very good fungicidal action which is better than that of the known fungicides.

Y is preferably methylene, ethylene, ethenylene, ethynylene, O, S, methyleneoxy, ethyleneoxy, oxymethylene, thiomethylene, carbonyloxy, oxycarbonyl, carbonyloxymethylene or --HN--CO--O--.

Z is preferably hydrogen, halogen (e.g. fluorine, chlorine or bromine), C₁ -C₁₈ -alkyl, (e.g. methyl, ethyl, n-or isopropyl, n-, sec-, iso- or tert-butyl, 3-methylbutyl, 2,2-dimethylpropyl, 1,1-dimethylpropyl, 3-hexyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-pentadecyl, n-heptadecyl or 2,6-dimethylhept-1-yl), cyanomethyl, C₂ -C₉ -alkenyl (e.g. vinyl, prop-2-en-2-yl, prop-1-en-1-yl, but-2-en-2-yl, 2-methylprop-1-en-1-yl, allyl, but-2-en-1-yl, 3-methylbut-2-en-1yl, penta-1,3-dien-1-yl, 2,6-dimethylhepta-1,5-dien-1-yl or 2,6-dimethylhept-5-en-1-yl); C₂ -alkynyl (e.g. ethynyl or 2-phenylethynyl), C₁ - or C₂ -alkoxy-C₁ - or -C₂ -alkyl (methoxymethyl, ethoxymethyl or 1-methoxyethyl), C₃ -C₆ -cycloalkyl (e.g. cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or 1-methylcyclopropyl), and the following substituted cyclopropyl radicals being examples:

2,2-dichloro-1-methylcyclopropyl (A1)

2,2-dichloro-3,3-dimethylcyclopropyl (A2)

2,2,3,3-tetramethylcyclopropyl (A3)

2-(2'-methyl-1'-propenyl)-3,3-dimethylcyclopropyl (A4)

2-(2',2'-difluorovinyl)-3,3-dimethylcyclopropyl (A5)

2-(2',2'-dichlorovinyl)-3,3-dimethylcyclopropyl (A6)

2-(2',2'-dibromovinyl)-3,3-dimethylcyclopropyl (A7)

2-phenylcyclopropyl (A8)

2-(4'-chlorophenyl)-cyclopropyl (A9)

2,2-dichloro-3-phenylcyclopropyl (A10)

2-carbomethoxycyclopropyl (A11)

or halo-C₁ - or C₂ -alkyl (e.g. chloromethyl, 1-chloroethyl, dichloromethyl, trichloromethyl, bromomethyl or trifluoromethyl), phenyl, substituted phenyl, such as halophenyl (e.g. 2-fluoro, 3-fluoro-, 4-fluoro-, 6-fluoro-, 2-chloro-, 2,4-difluoro-, 2,6-difluoro, 2,3,4,5,6-pentafluoro-, 3-chloro-, 4-chloro-, 2,4-dichloro-, 2,5-dichloro-, 2,6-dichloro-, 3,4-dichloro-, 3,5-dichloro-, 2,4,5-trichloro-, 2,3,4,5,6-pentachloro-, 2-bromo-, 3-bromo-, or 4-bromophenyl);

C₁ -C₄ -alkylphenyl (e.g. 2-methyl-, 3-methyl-, 4-methyl-, 2,3-dimethyl-, 2,4-dimethyl-, 2,5-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl-, 3,5-dimethyl-, 2,4,6-trimethyl-or 4-tert-butylphenyl); arylphenyl (e.g. 2-phenyl- or 4-phenylphenyl); halo-C₁ -alkylphenyl (e.g. 2-trifluoro-, 3-trifluoro-or 4-trifluoromethylphenyl); C₁ -C₄ -alkoxyphenyl (e.g. 2-methoxy-, 3-methoxy-, 4-methoxy-, 3,4-dimethoxy-, 3,4,5-trimethoxy- or 4-tert-butoxyphenyl); 2-, 3- or 4-phenoxyphenyl;

Substituted benzyl (e.g. halobenzyl, such as 2-fluoro-, 3-fluoro-, 4-fluoro-, 2-chloro-, 3-chloro-, 4-chloro-, 2-chloro-, 6-fluoro-, 2,4-dichloro-, 2,6-dichloro-, 3,5-dichloro-, 2,4,6-trichloro-, 2-bromo-, 3-bromo-, 4-bromo-, 2-methyl-, 3-methyl-, 4-methyl-, 4-tert-butyl-, 2,4-dimethyl-, 2,6-dimethyl-, 2,4,6-trimethyl-, 2-methoxy-, 3-methoxy-, 4-methoxy-, 2-trifluoromethyl-, 3-trifluoromethyl-, 4-trifluoromethyl-, 4-tert-butoxy-, 4-phenoxy-or 4-phenylbenzyl, α-methyl-α-ethyl-, α-isopropyl-, α-hydroxy-, 2-methoxy-α-hydroxy-, 4-methoxy-α-hydroxy-, 3,4-dimethoxy-α-hydroxy-, 2-methoxy-α-methoxy-, 4-methoxy-α-methoxy- or 3,4-dimethoxy-α-methoxybenzyl); unsubstituted or substituted phenethyl (e.g. phenyl-, 1-methyl-2-phenyl-, 2-(para-tert-butylphenyl)-, 2-(para-tert-butylphenyl)-1-methyl-, 2-(ortho-chlorophenyl)-, 2-(meta-chlorophenyl)- or 2-(para-chlorophenyl)ethyl); unsubstituted or substituted or styryl (e.g. styryl or 2'-chloro-, 3'-chloro-, 4'-chloro-, 2',4'-dichloro-, 2'-fluoro, 4'-fluoro-, 2'-methyl-, 4' -methyl-, 4'-tert-butyl-, 2'-methoxy-, 4'-methoxy- or 4'-phenoxystyryl); phenyl-C₃ -C₆ -alkyl (e.g. 3-phenylpropyl, 2-methyl-3-phenylpropyl, 4-phenylbutyl, 5-phenylpentyl, 6-phenylhexyl or 3-(4'-tert-butylphenyl)-2-methylpropyl);

aryloxy, such as substituted phenoxy (e.g. 2-chloro-, 3-chloro-, 4-chloro-, 2-methyl-, 4-methyl-, 2-methoxy-, 4-methoxy-, 2-trifluoromethyl- or 4-trifluoromethylphenoxy); aryloxy-C₁ -C₆ -alkyl, such as unsubstituted or substituted phenoxymethyl (e.g. 2-chloro-, 4-chloro-, 2-methyl-, 4-methyl-, 2-methoxy-, 4-methoxy- or 4-tert-butylphenoxymethyl); unsubstituted or substituted phenoxyethyl (e.g. 2-chloro-, 4-chloro-, 4-fluoro-, 2-methyl-, 4-methyl-, 2-methoxy-, 4-methoxy- or 4-tert-butylphenoxyethyl), unsubstituted or substituted C₃ -C₆ -phenoxyalkyl (e.g. phenoxypropyl, 3-(ortho-chlorophenoxy)-propyl, 3-(para-chlorophenoxy)-propyl, 4-phenoxybutyl, 4-(ortho-chlorophenoxy)-butyl, 4-(para-chlorophenoxy)-butyl, 5-phenoxypentyl, 5-(ortho-chlorophenoxy)-pentyl, 5-(para-chlorophenoxy)-pentyl or 6-phenoxyhexyl); phenoxyethoxy; methoxycarbonyl or tert-butoxycarbonyl; unsubstituted or substituted hetaryl (e.g. furyl, 2-furyl, 3-furyl, 5-nitro-2- and -3-furyl, 5-chloro-2- and -3-furyl, benzofuran-2- and -3-yl, thienyl, 2-thienyl, 3-thienyl, 5-nitro-2- and -3-thienyl, 5-chloro- 2-and -3-thienyl and benzothien-2- and -3-yl);

N-methylpyrrol-2- and -3-yl, N-methylpyrazol-3-, -4- and -5-yl, N-methylimidazol-2-, -4- and -5-yl, 1-methyl-1,2,3-triazol-4- and -5-yl, 1-methyl-1,2,4-triazol-3- and -5-yl, 1-methyltetrazol-5-yl, isoxazol-3-, -4- and -5-yl, benzisoxazol-3-yl, benzoxazol-2-yl, oxazol-2-, -4- and -5-yl, thiazol-2-, -4- and -5-yl, benzothiazol-2-yl, benzoisothiazol-3-yl, isothiazol-3-, -4- and -5-yl, 1,2,3-thiadiazol-4-yl, 1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazol-3-yl or 1,3-thiazolo[4,5-b]pyridin-2-yl) and substituted hetarylalkenyl (e.g. 2-(2'- and 3'-furyl)-, 2-(5'-nitro-2'- and -3'-furyl)-, 2-(2'- and 3'-thienyl)-and 2-(5'-nitro-2'- and -3'-thienyl)-ethenyl).

The compounds of the formula I can be prepared, for example, by the reactions shown in Scheme 1. ##STR3##

The phenylacetates of the formula II are converted in a conventional manner via the 3-aryl-2-oxosuccinates III into the methyl α-arylacrylates I (cf. E. Galantay et al., J. Org. Chem. 35 (1970), 4277). For this purpose, the phenylacetate (II) is acylated with a dialkyl oxalate with the aid of a base, e.g. sodium methylate or sodium ethylate, to give the diesters III and the latter are subjected to an addition reaction with formaldehyde. By hydrolysis with an aqueous base, e.g. potassium carbonate, the atropaic acid derivatives I are obtained. The compounds of the formula I can be prepared directly from phenylacetates II with paraformaldehyde, potassium carbonate and a catalytic amount of phase transfer catalyst, e.g. tetrabutylammonium iodide, in, for example, toluene [cf. W. Seitz and A. Michel, DE 3 317 356].

The α-ketocarboxylates of the formula IV can be converted into the acrylates of the formula I by a Wittig reaction with methylenetriphenylphosphorane in a conventional manner in the presence of a base, e.g. n-butyllithium, potassium tert-butylate, sodium hydride or sodium methylate (cf. G. Wittig and U. Schollkopf, Org. Synth., Coll. Vol. V (1973), 751).

Preparation of the α-ketoesters of the formula IV is known (EP 178826).

For example, the aromatic Grignard compounds VII are reacted with imidazolidenes of the formula VIII (J. S. Nimitz and H. S. Mosher, J. Org. Chem. 46 (1981), 211), where Y and Z have the abovementioned meanings. ##STR4##

The oxidation of substituted acetophenones (IX) with potassium permanganate in pyridine/water/potassium hydroxide ##STR5## (cf. J. W. F. McOmie and S. D. Thata, J. Chem. Soc. 1965, 5298) gives the phenylketoacids X, which can be esterified with, for example, methyl chloroformate/triethylamine to give the α-ketoesters IV (cf. J. M. Domagala, Tetrahedron Lett. 21 (1980), 4957).

The benzyl cyanides V can be converted into the α-arylacrylonitriles of the formula VI by treating them with a base, e.g. sodium methylate, and formaldehyde (cf. J. M. Stewart and C. H. Chang, J. Org. Chem. 21 (1956), 635).

The nitriles VI are converted into the acrylates of the formula I with a methanolic mineral acid, e.g. hydrochloric acid or sulfuric acid (cf. E. N. Zil'berman, Russ. Chem. Rev. 31 (1962), 615).

The Examples which follow illustrate the preparation of the novel compounds of the formula I.

EXAMPLE 1 Preparation of methyl 2-[2'-cinnamoyloxymethyl)-phenyl]acrylate (No. 866) a) Preparation of methyl ortho-bromomethylphenylglyoxalate

50.0 g (0.28 mole) of methyl ortho-methylphenylglyoxalate are dissolved in 3 liters of carbon tetrachloride, together with 50.0 g (0.28 mole) of freshly crystallized N-bromosuccinimide. The reaction mixture is exposed to a 300 W Hg vapor lamp for one hour and is evaporated down to 1 liter, the organic phase is washed with 3×200 ml of water and dried over sodium sulfate, the solvent is distilled off and the residue is chromatographed over silica gel with 1:9 methyl tert-butyl ether/hexane. 10 g of the ketoesters (II, YZ=CH₃) and 21.1 g of the benzyl bromide (II, Y-Z=CH₂ Br) (37%, based on converted ketoester) are obtained as a yellow oil.

¹ H (CDCl₃): δ=3.97(s,3H), 4.90(s,2H), 7.4-7.8(m,4H) IR (film): 2955, 1740, 1690, 1435, 1318, 1207, 999 cm⁻¹.

b) Preparation of methyl 2-(cinnamoylmethyl)-phenylglyoxalate

10.4 g (56 millimoles) of potassium transcinnamate and 12.0 g (47 millimoles) of methyl orthobromomethylphenylglyoxalate are dissolved in 250 ml of N-methylpyrrolidone, a pinch of potassium iodide is added and the mixture is stirred for 15 hours at room temperature (23° C.). Thereafter, the mixture is poured onto 500 ml of ice water and extracted with 3×200 ml of methyl tert-butyl ether and the organic phase is washed with water, dried over sodium sulfate and evaporated down in a rotary evaporator. The yield of ketoester is 15.0 g (99%). Thin layer chromatographic analysis shows that it is virtually pure.

¹ H-NMR (CDCl₃): δ=3.97 (s, 3H), 5.62 (s, 2H); 6.55 (d, J=10 Hz; 1H); 7.3-7.85 (m, 9H); 7.77 (d, J=10 Hz, 1H) IR (film): 1728, 1688, 1638, 1210, 1168, 998, 978, 765 cm⁻¹.

c) Preparation of methyl 2-[2'-(cinnamoyloxymethyl)-phenyl]-acrylate (No. 866)

10.5 g (26 millimoles) of methyltriphenylphosphonium iodide in 100 ml of anhydrous tetrahydrofuran are initially taken under a nitrogen atmosphere. 16.5 ml of a 1.6M solution of n-butyllithium in n-hexane are added dropwise at 0° C. and stirring is continued for 1 hour at 0° C. After the mixture has been cooled to -78° C., 7.5 g (23 millimoles) of the ketoester obtained according to b), in 50 ml of tetrahydrofuran, are slowly added dropwise. The mixture is allowed to reach room temperature and is stirred for a further 12 hours. It is poured into ammonium chloride solution and extracted with methyl tert-butyl ether. The organic phases are washed with water, dried over sodium sulfate and evaporated down. The product is obtained by column chromatography over silica gel using 1:9 methyl tert-butyl ether/n-hexane. 2.1 g (28%) of the abovementioned acrylate are obtained as an oil.

¹ H-NMR (CDCl₃): δ=3.75 (s, 3H); 5.18 (s, 2H); 5.8 (d, J=1 Hz, 1H); 6.42 (d, J=10 Hz, 1H); 6.60 (d, J=1 Hz, 1H); 7.15-7.60 (m, 9H); 7.68 (d, J=10 Hz; 1H).

IR (film): 1719, 1637, 1311, 1204, 1164, 768 cm⁻¹.

EXAMPLE 2 Preparation of the Intermediates Preparation of methyl 2-methylphenylglyoxalate

1.4 g (10 millimoles) of ortho-methylacetophenone, 2.0 g of potassium hydroxide, 200 ml of pyridine and 100 ml of water are initially taken at +10° C. 5 g of potassium permanganate in 250 ml of water are added dropwise and the mixture is stirred for 2 hours at this temperature. Thereafter, sodium bisulfite solution is added dropwise until the red coloration of the mixture vanishes. The mixture is filtered, the filtrate is acidified with concentrated hydrochloric acid and filtered again and this filtrate is extracted with 5×50 ml of methyl tert-butyl ether. The organic phase is dried over sodium sulfate and evaporated down and the residue is then directly reacted further (ratio of ketoacid to benzoic acid 8-9:1 according to ¹ H-NMR). 2.0 g of the above mixture in 20 ml of dichloromethane are initially taken and 1.6 g (16 millimoles) of triethylamine are added. 1.5 g (16 millimoles) of methyl chloroformate are added dropwise at room temperature. After 1 hour at this temperature, the mixture is extracted with phosphate buffer (pH 7) and evaporation and distillation are carried out.

Bp. 95°-99° C./0.4 mbar; yield: 0.92 g (51%).

IR (film): 1740, 1686, 1602, 1457, 1317, 1285, 1203, 1002, 739 cm⁻¹.

EXAMPLE 3 Preparation of methyl 2-[2'-(benzyloxyphenyl]-acrylate (No. 446)

25.6 g (0.10 mole) of methyl ortho-benzyloxyphenylacetate, 4.5 g (0.15 mole) of paraformaldehyde, 23.5 g (0.16 mole) of potassium carbonate and 600 mg (2 millimoles) of tetrabutylammonium iodide are added to 50 ml of toluene. The mixture is stirred for 3-4 hours at 80°-85° C., after which it is cooled and 50 ml of water are added. The mixture is shaken, the phases are separated, the aqueous phase is extracted with 2×50 ml of toluene and the toluene and the organic phase are extracted with 2×50 ml of saturated sodium chloride solution. Drying with Na₂ SO₄ and evaporation give a yellowish oil, which is chromatographed over silica gel using 1:2 methyl tert-butyl ether/hexane. Yield: 16.4 g (61%).

IR (film): 1727, 1602, 1495, 1451, 1276, 1242, 1268, 753, 735, 696 cm⁻¹.

¹ H-NMR (CDCl₃): δ=3.60 (s, 3H); 5.07 (s, 2H); 5.23 (d, J=1 Hz; 1H); 6.26 (d, J=1 Hz; 1H); 6.8-7.0 (m, 2H); 7.1-7.4 (m, 7H).

EXAMPLE 4 Preparation of 2'(2'-methoxycarbonylethen-1'-yl)-benzyltriphenylphosphonium bromide (No. 926)

14 g (80 millimoles) of methyl 2-(2'-methylphenyl)-acrylate, 28.5 g (160 millimoles) of N-bromosuccinimide and 500 ml of carbon tetrachloride are combined and the refluxed mixture is exposed for 3 hours to a mercury vapor lamp (300 W). The mixture is cooled, washed with water, dried with sodium sulfate and then evaporated down. The crude product (methyl 2-(2'-bromomethylphenyl)-acrylate (No. 925)) is dissolved in 500 ml of tetrahydrofuran, 21 g (80 millimoles) of triphenylphosphine are added and the mixture is kept for 15 hours at 23° C. and the boiled for 4 hours at 70° C. The mixture is cooled and filtered under suction, and the residue is washed with methyl tert-butyl ether and dried under reduced pressure to give 16.0 g (39%) of a white powder of melting point 145°-147° C.

¹ H-NMR (CDCl₃ ; No. 925): δ=3.78 (s, 3H); 4.42 (s, 2H); 5.90 (d, J=1 Hz; 1H); 6.65 (d, J=1 Hz, 1H); 7.1-7.5 (m, 4H).

¹ H-NMR (CDCl₃ ; No. 926): δ=3.62 (s, 3H); 5.07 (sbr, 1H); 5.15 (d, J=1 Hz, 2H); 6.27 (sbr; 1H); 7.0-7.85 (m, 19H).

    __________________________________________________________________________     No.  Z                         Y              Data                             __________________________________________________________________________     1    H                         CHCH                                            2    CH.sub.3                  CHCH                                            3    C.sub.2 H.sub.5           CHCH                                            4    n-C.sub.3 H.sub.7         CHCH                                            5    iso-C.sub.3 H.sub.7       CHCH                                            6    n-C.sub.4 H.sub.9         CHCH                                            7    (CH.sub.3).sub.2 CHCH.sub.2                                                                              CHCH                                            8    CH.sub.3 CH.sub.2 CH(CH.sub.3)                                                                           CHCH                                            9    tert.C.sub.4 H.sub.9      CHCH                                            10   CH.sub.3 CH.sub.2 C(CH.sub.3).sub.2                                                                      CHCH                                            11   (CH.sub.3).sub.2 CCH.sub.2                                                                               CHCH                                            12   (CH.sub.3).sub.2 CHCH.sub.2 CH.sub.2                                                                     CHCH                                            13   CH.sub.3 CH.sub.2 CH.sub.2 CH(C.sub.2 H.sub.5)                                                           CHCH                                            14   n-C.sub.5 H.sub.11        CHCH                                            15   n-C.sub.6 H.sub.13        CHCH                                            16   n-C.sub.7 H.sub.15        CHCH                                            17   n-C.sub.8 H.sub.17        CHCH                                            18   n-C.sub.9 H.sub.19        CHCH                                            19   n-C.sub.10 H.sub.21       CHCH                                            20   n-C.sub.15 H.sub.31       CHCH                                            21   n-C.sub.17 H.sub.35       CHCH                                            22   CH.sub.2CH                CHCH                                            23   CH.sub.2C(CH.sub.3)       CHCH                                            24   CH.sub.3 CHCH             CHCH                                            25   CH.sub.3 CHC(CH.sub.3)    CHCH                                            26   (CH.sub.3).sub.2 CCH      CHCH                                            27   CH.sub.2CHCH.sub.2        CHCH                                            28   CH.sub.3 CHCHCH.sub.2     CHCH                                            29   (CH.sub.3).sub.2 CCHCH.sub.2                                                                             CHCH                                            30   CH.sub.3 CHCHCHCH         CHCH                                            31   (CH.sub.3).sub.2 CCHCH.sub.2 CH.sub.2 C(CH.sub.3)CH                                                      CHCH                                            32   (CH.sub.3).sub.2 CHCH.sub.2 CH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2                                       CHCH                                            33   (CH.sub.3).sub.2 CCHCH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2                                               CHCH                                            34   HCC                       CHCH                                            35   C.sub.6 H.sub.5CC         CHCH                                            36   CH.sub.3 OCH.sub.2        CHCH                                            37   C.sub.2 H.sub.5 OCH.sub.2 CHCH                                            38   CH.sub.3 CH(OCH.sub.3)    CHCH                                            39   CNCH.sub.2                CHCH                                            40   cyclopropyl               CHCH                                            41   cyclobutyl                CHCH                                            42   cyclopentyl               CHCH                                            43   cyclohexyl                CHCH                                            44   1-methylcyclopropyl       CHCH                                            45   2,2-dichloro-1-methyl-cyclopropyl                                                                        CHCH                                            46   2,2-dichloro-3,3-dimethyl-cyclopropyl                                                                    CHCH                                            47   2,2,3,3-tetramethylcyclopropyl                                                                           CHCH                                            48   2-(2'-methyl-1'-propenyl-)-3,3-dimethylcyclopropyl                                                       CHCH                                            49   2-(2',2'-difluorovinyl)-3,3-dimethylcyclopropyl                                                          CHCH                                            50   2-(2',2'-dichlorovinyl)-3,3-dimethylcyclopropyl                                                          CHCH                                            51   2-(2',2'dibromovinyl)-3,3-dimethylcyclopropyl                                                            CHCH                                            52   2-phenylcyclopropyl       CHCH                                            53   2-(4'-chlorophenyl)cyclopropyl                                                                           CHCH                                            54   2,2-dichloro-3-phenylcyclopropyl                                                                         CHCH                                            55   2-carbomethoxy-cyclopropyl                                                                               CHCH                                            56   ClCH.sub.2                CHCH                                            57   Cl.sub.2 CH               CHCH                                            58   Cl.sub.3 C                CHCH                                            59   BrCH.sub.2                CHCH                                            60   CF.sub.3                  CHCH                                            61   CH.sub.3 CH(Cl)           CHCH                                            62   C.sub.6 H.sub.5 (phenyl)  CHCH                                            63   2-CH.sub.3C.sub.6 H.sub.4 CHCH                                            64   3-CH.sub.3C.sub.6 H.sub.4 CHCH                                            65   4-CH.sub.3C.sub.6 H.sub.4 CHCH                                            66   2,3-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      CHCH                                            67   2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      CHCH                                            68   2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      CHCH                                            69   3,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      CHCH                                            70   3,5-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      CHCH                                            71   2,4,6-(CH.sub.3).sub.2C.sub.6 H.sub.2                                                                    CHCH                                            72   4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4                                                                       CHCH                                            73   2-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                                         CHCH                                            73   2-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                                         CHCH                                            74   4-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                                         CHCH                                            75   2-ClC.sub.6 H.sub.4       CHCH                                            76   3-ClC.sub.6 H.sub.4       CHCH                                            77   4-ClC.sub.6 H.sub.4       CHCH                                            78   2,4-Cl.sub.2C.sub.6 H.sub. 3                                                                             CHCH                                            79   2,5-Cl.sub.2C.sub.6 H.sub.3                                                                              CHCH                                            80   2,6-Cl.sub.2C.sub.6 H.sub.3                                                                              CHCH                                            81   3,4-Cl.sub.2C.sub.6 H.sub.3                                                                              CHCH                                            82   3,5-Cl.sub.2C.sub.6 H.sub.3                                                                              CHCH                                            83   2,4,5-Cl.sub.3C.sub.6 H.sub.2                                                                            CHCH                                            84   2,3,4,5,6-Cl.sub.5C.sub.6 CHCH                                            85   6-F,2-ClC.sub.6 H.sub.3   CHCH                                            86   2-FC.sub.6 H.sub.4        CHCH                                            87   3-FC.sub.6 H.sub.4        CHCH                                            88   4-FC.sub.6 H.sub.4        CHCH                                            89   2,4-F.sub.2C.sub.6 H.sub.3                                                                               CHCH                                            90   2,6-F.sub.2C.sub.6 H.sub.3                                                                               CHCH                                            91   2,3,4,5,6-F.sub.5C.sub.6  CHCH                                            92   2-BrC.sub.6 H.sub.4       CHCH                                            93   3-BrC.sub.6 H.sub.4       CHCH                                            94   4-BrC.sub.6 H.sub.4       CHCH                                            95   2-CF.sub.3C.sub.6 H.sub.4 CHCH                                            96   3-CF.sub.3C.sub.6 H.sub.4 CHCH                                            97   4-CF.sub.3C.sub.6 H.sub.4  CHCH                                           98   2-OCH.sub.3C.sub.6 H.sub.4                                                                               CHCH                                            99   3-OCH.sub.3C.sub.6 H.sub.4                                                                               CHCH                                            100  4-OCH.sub.3C.sub.6 H.sub.4                                                                               CHCH                                            101  3,4-(OCH.sub.3).sub.2C.sub.6 H.sub.3                                                                     CHCH                                            102  3,4,5-(OCH.sub.3).sub.3C.sub.6 H.sub.2                                                                   CHCH                                            103  4-t-C.sub.4 H.sub.9 OC.sub.6 H.sub.4                                                                     CHCH                                            104  2-phenoxy-C.sub.6 H.sub.4 CHCH                                            105  3-phenoxy-C.sub.6 H.sub.4 CHCH                                            106  4-phenoxy-C.sub.6 H.sub.4 CHCH                                            107  C.sub.6 H.sub.5CH.sub.2   CHCH                                            108  2-FC.sub.6 H.sub.4CH.sub.2                                                                               CHCH                                            109  3-FC.sub.6 H.sub.4CH.sub.2                                                                               CHCH                                            110  4-FC.sub.6 H.sub.4CH.sub.2                                                                               CHCH                                            111  2-ClC.sub.6 H.sub.4CH.sub.2                                                                              CHCH                                            112  3-ClC.sub.6 H.sub.4CH.sub.2                                                                              CHCH                                            113  4-ClC.sub.6 H.sub.4CH.sub.2                                                                              CHCH                                            114  2-Cl, 6FC.sub.6 H.sub.3CH.sub.2                                                                          CHCH                                            115  2,4-Cl.sub.2C.sub.6 H.sub.3CH.sub.2                                                                      CHCH                                            116  2,6-Cl.sub.2C.sub.6 H.sub.3CH.sub.2                                                                      CHCH                                            117  3,5-Cl.sub.2C.sub.6 H.sub.3CH.sub.2                                                                      CHCH                                            118  2,4,6-Cl.sub.3C.sub.6 H.sub.2CH.sub.2                                                                    CHCH                                            119  2-CH.sub.3C.sub.6 H.sub.4CH.sub.2                                                                        CHCH                                            120  3-CH.sub.3C.sub.6 H.sub.4CH.sub.2                                                                        CHCH                                            121  4-CH.sub.3C.sub.6 H.sub.4CH.sub.2                                                                        CHCH                                            122  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2                                                               CHCH                                            123  2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3CH.sub.2                                                              CHCH                                            124  2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3CH.sub.2                                                              CHCH                                            125  2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2CH.sub.2                                                            CHCH                                            126  2-OCH.sub.3C.sub.6 H.sub.4CH.sub.2                                                                       CHCH                                            127  3-OCH.sub.3C.sub.6 H.sub.4CH.sub.2                                                                       CHCH                                            128  4-OCH.sub.3C.sub.6 H.sub.4CH.sub.2                                                                       CHCH                                            129  2-CF.sub.3C.sub.6 H.sub.4CH.sub.2                                                                        CH CH                                           130  3-CF.sub.3C.sub.6 H.sub.4CH.sub.2                                                                        CHCH                                            131  4-CF.sub.3C.sub.6 H.sub.4CH.sub.2                                                                        CHCH                                            132  4-O-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2                                                             CHCH                                            133  4-OC.sub.6 H.sub.5C.sub.6 H.sub.4CH.sub.2                                                                CHCH                                            134  4-C.sub.6 H.sub.5C.sub.6 H.sub.4CH.sub.2                                                                 CHCH                                            135  2-BrC.sub.6 H.sub.4CH.sub.2                                                                              CHCH                                            136  3-BrC.sub.6 H.sub.4CH.sub.2                                                                              CHCH                                            137  4-BrC.sub.6 H.sub.4CH.sub.2                                                                              CHCH                                            138  C.sub.6 H.sub.5CH(CH.sub.3)                                                                              CHCH                                            139  C.sub.6 H.sub.5CH(C.sub.2 H.sub.5)                                                                       CHCH                                            140  C.sub.6 H.sub.5CH(iso-C.sub.3 H.sub.7)                                                                   CHCH                                            141  C.sub.6 H.sub.5CH(OH)     CHCH                                            142  2-OCH.sub.3C.sub.6 H.sub.4CH(OH)                                                                         CHCH                                            143  4-OCH.sub.3C.sub.6 H.sub.4CH(OH)                                                                         CHCH                                            144  3,4-(OCH.sub.3).sub.2C.sub.6 H.sub.3CH(OH)                                                               CHCH                                            145  2-OCH.sub. 3C.sub.6 H.sub.4CH(OCH.sub.3)                                                                 CHCH                                            146  4-OCH.sub.3C.sub.6 H.sub.4CH(OCH.sub.3)                                                                  CHCH                                            147  3,4-(OCH.sub.3).sub.2C.sub.6 H.sub.3CH(OCH.sub.3)                                                        CHCH                                            148  C.sub.6 H.sub.5CH.sub.2 CH.sub.2                                                                         CHCH                                            149  C.sub.6 H.sub.5CH.sub.2 CH(CH.sub.3)                                                                     CHCH                                            150  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH.sub.2                                                      CHCH                                            151  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH(CH.sub.3)                                                  CHCH                                            152  2-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.2                                                                     CHCH                                            153  3-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.2                                                                     CHCH                                            154  4-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.2                                                                     CHCH                                            155  C.sub.6 H.sub.5CHCH       CHCH                                            156  2-ClC.sub.6 H.sub.4CHCH   CHCH                                            157  3-ClC.sub.6 H.sub.4CHCH   CHCH                                            158  4-ClC.sub.6 H.sub.4CHCH   CHCH                                            159  2,4-Cl.sub.2C.sub.6 H.sub.3 CHCH                                                                         CHCH                                            160  2-FC.sub.6 H.sub.4CHCH    CHCH                                            161  4-FC.sub.6 H.sub.4CHCH    CHCH                                            162  2-CH.sub.3C.sub.6 H.sub.4CHCH                                                                            CHCH                                            163  4-CH.sub.3C.sub.6 H.sub.4CHCH                                                                            CHCH                                            164  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CHCH                                                                   CHCH                                            165  2-OCH.sub.3C.sub.6 H.sub.4CHCH                                                                           CHCH                                            166  4-OCH.sub.3C.sub.6 H.sub.4CHCH                                                                           CHCH                                            167  4-phenoxy-C.sub.6 H.sub.4CHCH                                                                            CHCH                                            168  C.sub.6 H.sub.5(CH.sub.2).sub.3                                                                          CHCH                                            169  C.sub.6 H.sub.5CH.sub.2 CH(CH.sub.3)CH.sub.2                                                             CHCH                                            170  C.sub.6 H.sub.5(CH.sub.2).sub.4                                                                          CHCH                                            171  C.sub.6 H.sub.5(CH.sub.2).sub.5                                                                          CHCH                                            172  C.sub.6 H.sub.5(CH.sub.2).sub.6                                                                          CHCH                                            173  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH(CH.sub.3)CH.sub.2                                          CHCH                                            174  H                         CH.sub.2 CH.sub. 2                              175  CH.sub.3                  CH.sub.2 CH.sub.2                               176  C.sub.2 H.sub.5           CH.sub.2 CH.sub.2                               177  n-C.sub.3 H.sub.7         CH.sub.2 CH.sub.2                               178  iso-C.sub.3 H.sub.7       CH.sub.2 CH.sub.2                               179  n-C.sub.4 H.sub.9         CH.sub.2 CH.sub.2                               180  (CH.sub.3).sub.2 CHCH.sub.2                                                                              CH.sub.2 CH.sub.2                               181  CH.sub.3 CH.sub.2 CH(CH.sub.3)                                                                           CH.sub.2 CH.sub.2                               182  tert.C.sub.4 H.sub.9      CH.sub.2 CH.sub.2                               183  CH.sub.3 CH.sub.2 C(CH.sub.3).sub.2                                                                      CH.sub.2 CH.sub.2                               184  (CH.sub.3).sub.3 CCH.sub.2                                                                               CH.sub.2 CH.sub.2                               185  (CH.sub.3).sub.2 CHCH.sub.2 CH.sub.2                                                                     CH.sub.2 CH.sub.2                               186  CH.sub.3 CH.sub.2 CH.sub.2 CH(C.sub.2 H.sub.5)                                                           CH.sub.2 CH.sub.2                               187  n-C.sub.5 H.sub.11        CH.sub.2 CH.sub.2                               188  n-C.sub.6 H.sub.13        CH.sub.2 CH.sub.2                               189  n-C.sub.7 H.sub.15        CH.sub.2 CH.sub.2                               190  n-C.sub.8 H.sub.17        CH.sub.2 CH.sub.2                               191  n-C.sub. 9 H.sub.19       CH.sub.2 CH.sub.2                               192  n-C.sub.10 H.sub.21       CH.sub.2 CH.sub.2                               193  n-C.sub.15 H.sub.31       CH.sub.2 CH.sub.2                               194  n-C.sub.17 H.sub.35       CH.sub.2 CH.sub.2                               195  CH.sub.2CH                CH.sub.2 CH.sub.2                               196  CH.sub.2C(CH.sub.3)       CH.sub.2 CH.sub.2                               197  CH.sub.3 CHCH             CH.sub.2 CH.sub.2                               198  CH.sub.3 CHC(CH.sub.3)    CH.sub.2 CH.sub.2                               199  (CH.sub.3).sub.2 CCH      CH.sub.2 CH.sub.2                               200  CH.sub.2CHCH.sub.2        CH.sub.2 CH.sub.2                               201  CH.sub.3 CHCHCH.sub.2     CH.sub.2 CH.sub.2                               202  (CH.sub.3).sub.2 CCHCH.sub.2                                                                             CH.sub.2 CH.sub.2                               203  CH.sub.3 CHCHCHCH         CH.sub.2 CH.sub.2                               204  (CH.sub.3).sub.2 CCHCH.sub.2 CH.sub.2 C(CH.sub.3)CH                                                      CH.sub.2 CH.sub.2                               205  (CH.sub.3).sub.2 CHCH.sub.2 CH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2                                       CH.sub.2 CH.sub.2                               206  (CH.sub.3).sub.2 CHCH.sub.2 CH.sub. 2 CH(CH.sub.3)CH.sub.2                                               CH.sub.2 CH.sub.2                               207  HCC                       CH.sub.2 CH.sub.2                               208  C.sub.6 H.sub.5CC         CH.sub.2 CH.sub.2                               209  CH.sub.3 OCH.sub.2        CH.sub.2 CH.sub.2                               210  C.sub.2 H.sub.5 OCH.sub.2 CH.sub.2 CH.sub.2                               211  CH.sub.3 CH(OCH.sub.3)    CH.sub.2 CH.sub.2                               212  CNCH.sub.2                CH.sub.2 CH.sub.2                               213  cyclopropyl               CH.sub.2 CH.sub.2                               214  cyclobutyl                CH.sub.2 CH.sub.2                               215  cyclopentyl               CH.sub.2 CH.sub.2                               216  cyclohexyl                CH.sub.2 CH.sub.2                               217  1-methylcyclopropyl       CH.sub.2 CH.sub.2                               218  2,2-dichloro-1-methyl-cyclopropyl                                                                        CH.sub.2 CH.sub.2                               219  2,2-dichloro-3,3-dimethyl-cyclopropyl                                                                    CH.sub.2 CH.sub.2                               220  2,2,3,3-tetramethylcyclopropyl                                                                           CH.sub.2 CH.sub.2                               221  2-(2'-methyl-1'-propenyl-)-3,3dimethylcyclopropyl                                                        CH.sub.2 CH.sub.2                               222  2-(2',2'-difluorovinyl)-3,3-dimethylcyclopropyl                                                          CH.sub.2 CH.sub.2                               223  2-(2',2'-dichlorovinyl)-3,3-dimethylcyclopropyl                                                          CH.sub.2 CH.sub.2                               224  2-(2',2'-dibromovinyl)-3,3-dimethylcyclopropyl                                                           CH.sub.2 CH.sub.2                               225  2-phenylcyclopropyl       CH.sub.2 CH.sub.2                               226  2-(4'-chlorophenyl)cyclopropyl                                                                           CH.sub.2 CH.sub.2                               227  2,2-dichloro-3-phenylcyclopropyl                                                                         CH.sub.2 CH.sub.2                               228  2-carbomethoxy-cyclopropyl                                                                               CH.sub.2 CH.sub.2                               229  ClCH.sub.2                CH.sub.2 CH.sub.2                               230  Cl.sub.2 CH               CH.sub.2 CH.sub.2                               231  Cl.sub.3 C                CH.sub.2 CH.sub.2                               232  BrCH.sub.2                CH.sub.2 CH.sub.2                               233  CF.sub.3                  CH.sub.2 CH.sub.2                               234  CH.sub.3 CH(Cl)           CH.sub.2 CH.sub.2                               235  C.sub.6 H.sub.5 (phenyl)  CH.sub.2 CH.sub.2                               236  2-CH.sub.3C.sub.6 H.sub.4 CH.sub.2 CH.sub.2                               237  3-CH.sub.3C.sub.6 H.sub.4 CH.sub.2 CH.sub.2                               238  4-CH.sub.3C.sub.6 H.sub.4 CH.sub.2 CH.sub.2                               239  2,3-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      CH.sub.2 CH.sub.2                               240  2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      CH.sub.2 CH.sub.2                               241  2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      CH.sub.2 CH.sub.2                               242  3,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      CH.sub. 2 CH.sub.2                              243  3,5-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      CH.sub.2 CH.sub.2                               244  2,4,6-(CH.sub.3).sub.2C.sub.6 H.sub.2                                                                    CH.sub.2 CH.sub.2                               245  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4                                                                       CH.sub.2 CH.sub.2                               246  2-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                                         CH.sub.2 CH.sub.2                               247  4-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                                         CH.sub.2 CH.sub.2                               248  2-ClC.sub.6 H.sub.4       CH.sub.2 CH.sub.2                               249  3-ClC.sub.6 H.sub.4       CH.sub.2 CH.sub.2                               250  4-ClC.sub.6 H.sub.4       CH.sub.2 CH.sub.2                               251  2,4-Cl.sub.2C.sub.6 H.sub.3                                                                              CH.sub.2 CH.sub.2                               252  2,5-Cl.sub.2C.sub.6 H.sub.3                                                                              CH.sub.2 CH.sub.2                               253  2,6-Cl.sub.2C.sub.6 H.sub.3                                                                              CH.sub.2 CH.sub.2                               254  3,4-Cl.sub.2C.sub.6 H.sub.3                                                                              CH.sub.2 CH.sub.2                               255  3,5-Cl.sub.2C.sub.6 H.sub.3                                                                              CH.sub.2 CH.sub.2                               256  2,4,5-Cl.sub.3C.sub.6 H.sub.2                                                                            CH.sub.2 CH.sub.2                               257  2,3,4,5,6-Cl.sub.5C.sub.6 CH.sub. 2 CH.sub.2                              258  6-F,2ClC.sub.6 H.sub.3    CH.sub.2 CH.sub.2                               260  2-FC.sub.6 H.sub.4        CH.sub.2 CH.sub.2                               261  3-FC.sub.6 H.sub.4        CH.sub.2 CH.sub.2                               262  4-FC.sub.6 H.sub.4        CH.sub.2 CH.sub.2                               263  2,4-F.sub.2C.sub.6 H.sub.3                                                                               CH.sub.2 CH.sub.2                               264  2,6-F.sub.2C.sub.6 H.sub.3                                                                               CH.sub.2 CH.sub.2                               265  2,3,4,5,6-F.sub.5C.sub.6  CH.sub.2 CH.sub.2                               266  2-BrC.sub.6 H.sub.4       CH.sub.2 CH.sub.2                               267  3-BrC.sub.6 H.sub.4       CH.sub.2 CH.sub.2                               268  4-BrC.sub.6 H.sub.4       CH.sub.2 CH.sub.2                               269  2-CF.sub.3C.sub.6 H.sub.4 CH.sub.2 CH.sub.2                               270  3-CF.sub.3C.sub.6 H.sub.4 CH.sub.2 CH.sub.2                               271  4-CF.sub.3C.sub.6 H.sub.4 CH.sub.2 CH.sub.2                               272  2-OCH.sub.3C.sub.6 H.sub.4                                                                               CH.sub.2 CH.sub.2                               273  3-OCH.sub.3C.sub.6 H.sub.4                                                                               CH.sub.2 CH.sub.2                               277  4-t-C.sub.4 H.sub.9 OC.sub.6 H.sub. 4                                                                    CH.sub.2 CH.sub.2                               278  2-phenoxy-C.sub.6 H.sub.4 CH.sub.2 CH.sub.2                               279  3-phenoxy-C.sub.6 H.sub.4 CH.sub.2 CH.sub.2                               280  4-phenoxy-C.sub.6 H.sub.4 CH.sub.2 CH.sub.2                               281  C.sub.6 H.sub.5CH.sub.2   CH.sub.2 CH.sub.2                               282  2-FC.sub.6 H.sub.4CH.sub.2                                                                               CH.sub.2 CH.sub.2                               283  3-FC.sub.6 H.sub.4CH.sub.2                                                                               CH.sub.2 CH.sub.2                               284  4-FC.sub.6 H.sub.4CH.sub.2                                                                               CH.sub.2 CH.sub.2                               285  2-ClC.sub.6 H.sub.4CH.sub.2                                                                              CH.sub.2 CH.sub.2                               286  3-ClC.sub.6 H.sub.4CH.sub.2                                                                              CH.sub.2 CH.sub.2                               287  4-ClC.sub.6 H.sub.4CH.sub.2                                                                              CH.sub.2 CH.sub.2                               288  2-Cl,6FC.sub.6 H.sub.3CH.sub.2                                                                           CH.sub.2 CH.sub.2                               289  2,4-Cl.sub.2C.sub.6 H.sub.3CH.sub.2                                                                      CH.sub.2 CH.sub.2                               290  2,6-Cl.sub.2C.sub.6 H.sub.3CH.sub.2                                                                      CH.sub.2 CH.sub.2                               291  3,5-Cl.sub.2C.sub.6 H.sub.3CH.sub.2                                                                      CH.sub.2 CH.sub.2                               292  2,4,6-Cl.sub.3C.sub.6 H.sub.2CH.sub.2                                                                    CH.sub.2 CH.sub.2                               293  2-CH.sub.3C.sub.6 H.sub.4CH.sub.2                                                                        CH.sub.2 CH.sub.2                               294  3-CH.sub.3C.sub.6 H.sub.4CH.sub. 2                                                                       CH.sub.2 CH.sub.2                               295  4-CH.sub.3C.sub.6 H.sub.4CH.sub.2                                                                        CH.sub.2 CH.sub.2                               296  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2                                                               CH.sub.2 CH.sub.2                               297  2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3CH.sub.2                                                              CH.sub.2 CH.sub.2                               298  2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3CH.sub.2                                                              CH.sub.2 CH.sub.2                               299  2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2CH.sub.2                                                            CH.sub.2 CH.sub.2                               300  2-OCH.sub.3C.sub.6 H.sub.4CH.sub.2                                                                       CH.sub.2 CH.sub.2                               301  3-OCH.sub.3C.sub.6 H.sub.4CH.sub.2                                                                       CH.sub.2 CH.sub.2                               302  4-OCH.sub.3C.sub.6 H.sub.4CH.sub.2                                                                       CH.sub.2 CH.sub.2                               302  2-CF.sub.3C.sub.6 H.sub.4CH.sub.2                                                                        CH.sub.2 CH.sub.2                               303  3-CF.sub.3C.sub.6 H.sub.4CH.sub.2                                                                        CH.sub.2 CH.sub.2                               304  4-CF.sub.3C.sub.6 H.sub.4CH.sub.2                                                                        CH.sub.2 CH.sub.2                               305  4-O-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2                                                             CH.sub.2 CH.sub.2                               306  4-OC.sub. 6 H.sub.5C.sub.6 H.sub.4CH.sub.2                                                               CH.sub.2 CH.sub.2                               307  4-C.sub.6 H.sub.5C.sub.6 H.sub.4CH.sub.2                                                                 CH.sub.2 CH.sub.2                               308  2-BrC.sub.6 H.sub.4CH.sub.2                                                                              CH.sub.2 CH.sub.2                               309  3-BrC.sub.6 H.sub.4CH.sub.2                                                                              CH.sub.2 CH.sub.2                               310  4-BrC.sub.6 H.sub.4CH.sub.2                                                                              CH.sub.2 CH.sub.2                               311  C.sub.6 H.sub.5CH(CH.sub.3)                                                                              CH.sub.2 CH.sub.2                               312  C.sub.6 H.sub.5CH(C.sub.2 H.sub.5)                                                                       CH.sub.2 CH.sub.2                               313  C.sub.6 H.sub.5CH(iso-C.sub.3 H.sub.7)                                                                   CH.sub.2 CH.sub.2                               314  C.sub.6 H.sub.5CH(OH)     CH.sub.2 CH.sub.2                               315  2-OCH.sub.3C.sub.6 H.sub.4CH(OH)                                                                         CH.sub.2 CH.sub.2                               316  4-OCH.sub.3C.sub.6 H.sub.4CH(OH)                                                                         CH.sub.2 CH.sub.2                               317  3,4-(OCH.sub.3).sub.2C.sub.6 H.sub.3CH(OH)                                                               CH.sub.2 CH.sub.2                               318  2-OCH.sub.3C.sub.6 H.sub.4CH(OCH.sub.3)                                                                  CH.sub.2 CH.sub.2                               319  4-OCH.sub.3C.sub.6 H.sub.4CH(OCH.sub. 3)                                                                 CH.sub.2 CH.sub.2                               320  3,4-(OCH.sub.3).sub.2C.sub.6 H.sub.3CH(OCH.sub.3)                                                        CH.sub.2 CH.sub.2                               321  C.sub.6 H.sub.5CH.sub.2 CH.sub.2                                                                         CH.sub.2 CH.sub.2                               322  C.sub.6 H.sub.5CH.sub.2 CH(CH.sub.3)                                                                     CH.sub.2 CH.sub.2                               323  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH.sub.2                                                      CH.sub.2 CH.sub.2                               324  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH(CH.sub.3)                                                  CH.sub.2 CH.sub.2                               325  2-Cl-C.sub.6 H.sub.4CH.sub.2 CH.sub.2                                                                    CH.sub.2 CH.sub.2                               326  3-Cl-C.sub.6 H.sub.4CH.sub.2 CH.sub.2                                                                    CH.sub.2 CH.sub.2                               327  4-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.2                                                                     CH.sub.2 CH.sub.2                               328  C.sub.6 H.sub.5CHCH       CH.sub.2 CH.sub.2                               329  2-ClC.sub.6 H.sub.4CHCH   CH.sub.2 CH.sub.2                               330  3-ClC.sub.6 H.sub.4CHCH   CH.sub.2 CH.sub.2                               331  4-ClC.sub.6 H.sub.4CHCH   CH.sub.2 CH.sub.2                               332  2,4-Cl.sub.2 C.sub.6 H.sub.3CHCH                                                                         CH.sub.2 CH.sub.2                               333  2-FC.sub.6 H.sub.4CHCH    CH.sub.2 CH.sub.2                               334  4-FC.sub.6 H.sub.4CHCH    CH.sub.2 CH.sub.2                               335  2-CH.sub.3C.sub.6 H.sub.4CHCH                                                                            CH.sub.2 CH.sub.2                               336  4-CH.sub.3C.sub.6 H.sub.4CHCH                                                                            CH.sub.2 CH.sub.2                               337  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CHCH                                                                   CH.sub.2 CH.sub.2                               338  2-OCH.sub.3C.sub.6 H.sub.4CHCH                                                                           CH.sub.2 CH.sub.2                               339  4-OCH.sub.3C.sub.6 H.sub.4CHCH                                                                           CH.sub.2 CH.sub.2                               340  4-phenoxy-C.sub.6 H.sub.4CHCH                                                                            CH.sub.2 CH.sub.2                               341  C.sub.6 H.sub.5(CH.sub.2).sub.3                                                                          CH.sub.2 CH.sub.2                               342  C.sub.6 H.sub.5CH.sub.2 CH(CH.sub.3)CH.sub.2                                                             CH.sub.2 CH.sub.2                               343  C.sub.6 H.sub.5(CH.sub.2).sub.4                                                                          CH.sub.2 CH.sub.2                               344  C.sub.6 H.sub.5(CH.sub.2).sub.5                                                                          CH.sub.2 CH.sub.2                               345  C.sub.6 H.sub.5(CH.sub.2).sub. 6                                                                         CH.sub.2 CH.sub.2                               346  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH(CH.sub.3)CH.sub.2                                          CH.sub.2 CH.sub.2                               347  C.sub.6 H.sub.5 O         CH.sub.2 CH.sub.2                               348  2-ClC.sub.6 H.sub.4 O     CH.sub.2 CH.sub.2                               349  3-ClC.sub.6 H.sub.4 O     CH.sub.2 CH.sub.2                               350  4-ClC.sub.6 H.sub.4 O     CH.sub.2 CH.sub.2                               351  2-CH.sub.3C.sub.6 H.sub.4 O                                                                              CH.sub.2 CH.sub.2                               352  4-CH.sub.3C.sub.6 H.sub.4 O                                                                              CH.sub.2 CH.sub.2                               353  2-OCH.sub.3C.sub.6 H.sub.4 O                                                                             CH.sub.2 CH.sub.2                               354  4-OCH.sub.3C.sub.6 H.sub.4 O                                                                             CH.sub.2 CH.sub.2                               355  2-CF.sub.3C.sub.6 H.sub.4 O                                                                              CH.sub.2 CH.sub.2                               356  4-CF.sub.3C.sub.6 H.sub.4 O                                                                              CH.sub.2 CH.sub.2                               357  C.sub.6 H.sub.5 OCH.sub.2 CH.sub.2 CH.sub.2                               358  2-ClC.sub.6 H.sub.4 OCH.sub.2                                                                            CH.sub.2 CH.sub.2                               359  4-ClC.sub.6 H.sub.4 OCH.sub.2                                                                            CH.sub. 2 CH.sub.2                              360  2-CH.sub.3C.sub.6 H.sub.4 OCH.sub.2                                                                      CH.sub.2 CH.sub.2                               361  4-CH.sub.3C.sub.6 H.sub.4 OCH.sub.2                                                                      CH.sub.2 CH.sub.2                               362  2-OCH.sub.3C.sub.6 H.sub.4 OCH.sub.2                                                                     CH.sub.2 CH.sub.2                               363  4-OCH.sub.3C.sub.6 H.sub.4 OCH.sub.2                                                                     CH.sub.2 CH.sub.2                               364  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4 OCH.sub.2                                                             CH.sub.2 CH.sub.2                               365  C.sub.6 H.sub.5 OCH.sub.2 CH.sub.2                                                                       CH.sub.2 CH.sub.2                               366  2-ClC.sub.6 H.sub.4 OCH.sub.2 CH.sub.2                                                                   CH.sub.2 CH.sub.2                               367  4-ClC.sub.6 H.sub.4 OCH.sub.2 CH.sub.2                                                                   CH.sub.2 CH.sub.2                               368  4-FC.sub.6 H.sub.4 OCH.sub.2 CH.sub.2                                                                    CH.sub.2 CH.sub.2                               369  2-CH.sub.3C.sub.6 H.sub.4 OCH.sub.2 CH.sub.2                                                             CH.sub.2 CH.sub.2                               370  4-CH.sub.3C.sub.6 H.sub.4 OCH.sub.2 CH.sub.2                                                             CH.sub.2 CH.sub.2                               371  2-OCH.sub.3C.sub.6 H.sub.4 OCH.sub.2 CH.sub.2                                                            CH.sub.2 CH.sub.2                               372  4-OCH.sub.3C.sub.6 H.sub.4 OCH.sub.2 CH.sub.2                                                            CH.sub.2 CH.sub.2                               373  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4OCH.sub.2 CH.sub.2                                                     CH.sub.2 CH.sub.2                               374  C.sub.6 H.sub.5 O(CH.sub.2).sub.3                                                                        CH.sub.2 CH.sub.2                               375  2-ClC.sub.6 H.sub.4 O(CH.sub.2).sub.3                                                                    CH.sub.2 CH.sub.2                               376  4-ClC.sub.6 H.sub.4 O(CH.sub.2).sub.3                                                                    CH.sub.2 CH.sub.2                               377  C.sub.6 H.sub.5 O(CH.sub.2).sub.4                                                                        CH.sub.2 CH.sub.2                               378  2-ClC.sub.6 H.sub.4O(CH.sub.2).sub.4                                                                     CH.sub.2 CH.sub.2                               379  4-ClC.sub.6 H.sub.4O(CH.sub.2).sub.4                                                                     CH.sub.2 CH.sub.2                               380  C.sub.6 H.sub.5 O(CH.sub.2).sub.5                                                                        CH.sub.2 CH.sub.2                               381  2-ClC.sub.6 H.sub.4 O(CH.sub.2).sub.5                                                                    CH.sub.2 CH.sub.2                               382  4-ClC.sub.6 H.sub.4 O(CH.sub.2).sub.5                                                                    CH.sub.2 CH.sub.2                               383  C.sub.6 H.sub.5 O(CH.sub.2).sub.6                                                                        CH.sub.2 CH.sub.2                               384  C.sub.6 H.sub.5 OCH.sub.2 CH.sub.2 O                                                                     CH.sub.2 CH.sub.2                               385  H                         CH.sub.2 O                                      386  CH.sub.3                  CH.sub.2 O                                      387  C.sub.2 H.sub.5           CH.sub.2 O                                      388  n-C.sub.3 H.sub.7         CH.sub.2 O                                      389  iso-C.sub.3 H.sub.7       CH.sub.2 O                                      390  n-C.sub.4 H.sub.9         CH.sub.2 O                                      391  (CH.sub.3).sub.2 CHCH.sub.2                                                                              CH.sub.2 O                                      392  CH.sub.3 CH.sub.2 CH(CH.sub.3)                                                                           CH.sub.2 O                                      393  tert.C.sub.4 H.sub.9      CH.sub.2 O                                      394  CH.sub.3 CH.sub.2 C(CH.sub.3).sub.2                                                                      CH.sub.2 O                                      395  (CH.sub.3).sub.3 CCH.sub.2                                                                               CH.sub.2 O                                      396  (CH.sub.3).sub.2 CHCH.sub.2 CH.sub.2                                                                     CH.sub.2 O                                      397  CH.sub.3 CH.sub.2 CH.sub.2 CH(C.sub.2 H.sub.5)                                                           CH.sub.2 O                                      398  n-C.sub.5 H.sub.11        CH.sub.2 O                                      399  n-C.sub.6 H.sub.13        CH.sub.2 O                                      400  n-C.sub.7 H.sub.15        CH.sub.2 O                                      401  n-C.sub.8 H.sub.17        CH.sub.2 O                                      402  n-C.sub.9 H.sub.19        CH.sub.2 O                                      403  n-C.sub.10 H.sub.21       CH.sub.2 O                                      404  n-C.sub.15 H.sub.31       CH.sub.2 O                                      405  n-C.sub.17 H.sub.35       CH.sub.2 O                                      406  CH.sub.2CH                CH.sub.2 O                                      407  CH.sub.2C(CH.sub.3)       CH.sub.2 O                                      408  CH.sub.3 CHCH             CH.sub.2 O                                      409  CH.sub.3 CHC(CH.sub.3)    CH.sub.2 O                                      410  (CH.sub.3).sub.2 CCH      CH.sub.2 O                                      411  CH.sub.2CHCH.sub.2        CH.sub.2 O                                      412  CH.sub.3 CHCHCH.sub.2     CH.sub.2 O                                      413  (CH.sub.3).sub.2 CCHCH.sub.2                                                                             CH.sub.2 O                                      414  CH.sub.3 CHCHCHCH         CH.sub.2 O                                      415  (CH.sub.3).sub.2 CCHCH.sub.2 CH.sub.2 C(CH.sub.3)CH                                                      CH.sub.2 O                                      416  (CH.sub.3).sub.2 CHCH.sub.2 CH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2                                       CH.sub.2 O                                      417  (CH.sub.3).sub.2 CCHCH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2                                               CH.sub.2 O                                      418  HC C                      CH.sub.2 O                                      419  C.sub.6 H.sub.5CC         CH.sub.2 O                                      420  CH.sub.3 OCH.sub.2        CH.sub.2 O                                      421  C.sub.2 H.sub.5 OCH.sub.2 CH.sub.2 O                                      422  CH.sub.3 CH(OCH.sub.3)    CH.sub.2 O                                      423  CNCH.sub.2                CH.sub.2 O                                      424  cyclopropyl               CH.sub.2 O                                      425  cyclobutyl                CH.sub.2 O                                      426  cyclopentyl               CH.sub.2 O                                      427  cyclohexyl                CH.sub.2 O                                      428  1-methylcyclopropyl       CH.sub.2 O                                      429  2,2-dichloro-1-methyl-cyclopropyl                                                                        CH.sub.2 O                                      430  2,2-dichloro-3,3-dimethyl-cyclopropyl                                                                    CH.sub.2 O                                      431  2,2,3,3-tetramethylcyclopropyl                                                                           CH.sub.2 O                                      432  2-(2'-methyl-1'-propenyl-)-3,3-dimethylcyclopropyl                                                       CH.sub.2 O                                      433  2-(2',2'-difluorovinyl)-3,3-dimethylcyclopropyl                                                          CH.sub.2 O                                      434  2-(2',2'-dichlorovinyl)-3,3-dimethylcyclopropyl                                                          CH.sub.2 O                                      435  2-(2',2'-dibromovinyl)-3,3-dimethylcyclopropyl                                                           CH.sub.2 O                                      436  2-phenylcyclopropyl       CH.sub.2 O                                      437  2-(4'-chlorophenyl)cyclopropyl                                                                           CH.sub.2 O                                      438  2,2-dichloro-3-phenylcyclopropyl                                                                         CH.sub.2 O                                      439  2-carbomethoxy-cyclopropyl                                                                               CH.sub.2 O                                      440  Cl.sub.2 CH               CH.sub.2 O                                      441  Cl.sub.2 CH               CH.sub.2 O                                      442  Cl.sub.3 C                CH.sub.2 O                                      443  BrCH.sub.2                CH.sub.2 O                                      444  CF.sub.3                  CH.sub.2 O                                      445  CH.sub.3 CH(Cl)           CH.sub.2 O                                      446  C.sub.6 H.sub.5 (phenyl)  CH.sub.2 O     oil; IR (film):                                                                1727,1602,1495,1451,1276,                                                      1242,1208,753,735,696                                                          cm.sup.-1                        447  2-CH.sub.3C.sub.6 H.sub.4 CH.sub.2 O                                      448  3-CH.sub.3C.sub.6 H.sub.4 CH.sub.2 O     oil; IR (film):                                                                1738,1602,1495,1242,1160                                                       1018,753 cm.sup.-1               449  4-CH.sub.3C.sub.6 H.sub.4 CH.sub.2 O                                      450  2,3-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      CH.sub.2 O                                      451  2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      CH.sub.2 O                                      452  2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      CH.sub.2 O                                      453  3,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      CH.sub.2 O                                      454  3,5-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      CH.sub.2 O                                      455  2,4,6-(CH.sub.3).sub. 2C.sub.6 H.sub.2                                                                   CH.sub.2 O                                      456  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4                                                                       CH.sub.2 O                                      457  2-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                                         CH.sub.2 O                                      458  4-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                                         CH.sub.2 O                                      459  2-ClC.sub.6 H.sub.4       CH.sub.2 O                                      460  3-ClC.sub.6 H.sub.4       CH.sub.2 O     oil; IR (film): 1726,1491                                                      1451,1210,753 cm.sup.-1          461  4-ClC.sub.6 H.sub.4       CH.sub.2 O                                      462  2,4-Cl.sub.2C.sub.6 H.sub.3                                                                              CH.sub.2 O                                      463  2,5-Cl.sub.2C.sub.6 H.sub.3                                                                              CH.sub.2 O                                      464  2,6-Cl.sub.2C.sub.6 H.sub.3                                                                              CH.sub.2 O                                      465  3,4-Cl.sub.2C.sub.6 H.sub.3                                                                              CH.sub.2 O                                      466  3,5-Cl.sub.2C.sub.6 H.sub.3                                                                              CH.sub.2 O                                      467  2,4,5-Cl.sub.3C.sub.6 H.sub.2                                                                            CH.sub.2 O                                      468  2,3,4,5,6-Cl.sub.5C.sub.6 CH.sub.2 O                                      469  6-F,2-ClC.sub.6 H.sub.3   CH.sub.2 O                                      470  2-FC.sub.6 H.sub.4        CH.sub.2 O                                      471  3-FC.sub.6 H.sub.4        CH.sub.2 O                                      472  2,4-F.sub.2C.sub.6 H.sub.3                                                                               CH.sub.2 O                                      473  2,6-F.sub.2C.sub.6 H.sub.3                                                                               CH.sub.2 O                                      474  2,6-F.sub.2C.sub.6 H.sub.3                                                                               CH.sub.2 O                                      475  2,3,4,5,6-E.sub.5C.sub.6  CH.sub.2 O                                      476  2-BrC.sub.6 H.sub.4       CH.sub.2 O                                      477  3-BrC.sub.6 H.sub.4       CH.sub.2 O                                      478  4-BrC.sub.6 H.sub.4       CH.sub.2 O                                      479  2-CF.sub.3C.sub.6 H.sub.4 CH.sub.2 O                                      480  3-CF.sub.3C.sub.6 H.sub.4 CH.sub.2 O                                      481  4-CF.sub.3C.sub.6 H.sub.4 CH.sub.2 O                                      482  2-OCH.sub.3C.sub.6 H.sub.4                                                                               CH.sub.2 O                                      483  3-OCH.sub.3C.sub.6 H.sub.4                                                                               CH.sub.2 O                                      484  4-OCH.sub.3C.sub.6 H.sub.4                                                                               CH.sub.2 O                                      485  3,4-(OCH.sub.3).sub.2C.sub.6 H.sub.3                                                                     CH.sub.2 O                                      486  3,4,5-(OCH.sub.3).sub.3C.sub.6 H.sub.2                                                                   CH.sub.2 O                                      487  4-t-C.sub.4 H.sub.9 OC.sub.6 H.sub.4                                                                     CH.sub.2 O                                      488  2-phenoxy-C.sub.6 H.sub.4 CH.sub.2 O                                      489  3-phenoxy-C.sub.6 H.sub.4 CH.sub.2 O                                      490  4-phenoxy-C.sub.6 H.sub.4 CH.sub.2 O                                      491  C.sub.6 H.sub.5CH.sub.2   CH.sub.2 O                                      492  2-FC.sub.6 H.sub.4CH.sub.2                                                                               CH.sub.2 O                                      493  3-FC.sub.6 H.sub.4CH.sub.2                                                                               CH.sub.2 O                                      494  4-FC.sub.6 H.sub.4CH.sub.2                                                                               CH.sub.2 O                                      495  2-ClC.sub.6 H.sub.4CH.sub.2                                                                              CH.sub.2 O                                      496  3-ClC.sub.6 H.sub.4CH.sub.2                                                                              CH.sub.2 O                                      497  4-ClC.sub.6 H.sub.4CH.sub.2                                                                              CH.sub.2 O                                      498  2-Cl,6FC.sub.6 H.sub.3CH.sub.2                                                                           CH.sub.2 O                                      499  2,4-Cl.sub.2C.sub.6 H.sub.3CH.sub.2                                                                      CH.sub.2 O                                      500  2,6-Cl.sub.2C.sub.6 H.sub.3CH.sub.2                                                                      CH.sub.2 O                                      501  3,5-Cl.sub.2C.sub.6 H.sub.3CH.sub.2                                                                      CH.sub.2 O                                      502  2,4,6-Cl.sub.3C.sub.6 H.sub.2CH.sub.2                                                                    CH.sub.2 O                                      503  2-CH.sub.3C.sub.6 H.sub.4CH.sub.2                                                                        CH.sub.2 O                                      504  3-CH.sub. 3C.sub.6 H.sub.4CH.sub.2                                                                       CH.sub.2 O                                      505  4-CH.sub.3C.sub.6 H.sub.4CH.sub.2                                                                        CH.sub.2 O                                      506  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2                                                               CH.sub.2 O                                      507  2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3CH.sub.2                                                              CH.sub.2 O                                      508  2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3CH.sub.2                                                              CH.sub.2 O                                      509  2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2CH.sub.2                                                            CH.sub.2 O                                      510  2-OCH.sub.3C.sub.6 H.sub.4CH.sub.2                                                                       CH.sub.2 O                                      511  3-OCH.sub.3C.sub.6 H.sub.4CH.sub.2                                                                       CH.sub.2 O                                      512  4-OCH.sub.3C.sub.6 H.sub.4CH.sub.2                                                                       CH.sub.2 O                                      513  2-CF.sub.3C.sub.6 H.sub.4CH.sub.2                                                                        CH.sub.2 O                                      514  3-CF.sub.3C.sub.6 H.sub.4CH.sub.2                                                                        CH.sub.2 O                                      515  4-CF.sub.3C.sub.6 H.sub.4CH.sub.2                                                                        CH.sub.2 O                                      516  4-O-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2                                                             CH.sub.2 O                                      517  4-OC.sub.6 H.sub.5C.sub.6 H.sub.4 CH.sub.2                                                               CH.sub.2 O                                      518  4-C.sub.6 H.sub.5C.sub.6 H.sub.4CH.sub.2                                                                 CH.sub.2 O                                      519  2-BrC.sub.6 H.sub.4CH.sub.2                                                                              CH.sub.2 O                                      520  3-BrC.sub.6 H.sub.4CH.sub.2                                                                              CH.sub.2 O                                      521  4-BrC.sub.6 H.sub.4CH.sub.2                                                                              CH.sub.2 O                                      522  C.sub.6 H.sub.5CH(CH.sub.3)                                                                              CH.sub.2 O                                      523  C.sub.6 H.sub.5CH(C.sub.2 H.sub.5)                                                                       CH.sub.2 O                                      524  C.sub.6 H.sub.5CH(iso-C.sub.3 H.sub.7)                                                                   CH.sub.2 O                                      525  C.sub.6 H.sub.5CH(OH)     CH.sub.2 O                                      526  2-OCH.sub.3C.sub.6 H.sub.4CH(OH)                                                                         CH.sub.2 O                                      527  4-OCH.sub.3C.sub.6 H.sub.4CH(OH)                                                                         CH.sub.2 O                                      528  3,4-(OCH.sub.3).sub.2C.sub.6 H.sub.3CH(OH)                                                               CH.sub.2 O                                      529  2-OCH.sub.3C.sub.6 H.sub.4CH(OCH.sub.3)                                                                  CH.sub.2 O                                      530  4-OCH.sub.3C.sub.6 H.sub.4CH(OCH.sub.3)                                                                  CH.sub.2 O                                      531  3,4-(OCH.sub.3).sub.2C.sub.6 H.sub.3CH(OCH.sub.3)                                                         CH.sub.2 O                                     532  C.sub.6 H.sub.5CH.sub.2 CH.sub.2                                                                         CH.sub.2 O                                      533  C.sub.6 H.sub.5CH.sub.2 CH(CH.sub.3)                                                                     CH.sub.2 O                                      534  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH.sub.2                                                      CH.sub.2 O                                      535  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH(CH.sub.3)                                                  CH.sub.2 O                                      536  2-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.2                                                                     CH.sub.2 O                                      537  3-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.2                                                                     CH.sub.2 O                                      538  4-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.2                                                                     CH.sub.2 O                                      539  C.sub.6 H.sub.5CHCH       CH.sub.2 O                                      540  2-ClC.sub.6 H.sub.4CHCH   CH.sub.2 O                                      541  3-ClC.sub.6 H.sub.4CHCH   CH.sub.2 O                                      542  4-ClC.sub.6 H.sub.4CHCH   CH.sub.2 O                                      543  2,4-Cl.sub.2C.sub.6 H.sub.3CHCH                                                                          CH.sub.2 O                                      545  2-FC.sub.6 H.sub.4CHCH    CH.sub.2 O                                      546  4-FC.sub.6 H.sub.4CH CH   CH.sub.2 O                                      547  2-CH.sub.3C.sub.6 H.sub.4CHCH                                                                            CH.sub.2 O                                      548  4-CH.sub.3C.sub.6 H.sub.4CHCH                                                                            CH.sub.2 O                                      549  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CHCH                                                                   CH.sub.2 O                                      550  2-OCH.sub.3C.sub.6 H.sub.4CHCH                                                                           CH.sub.2 O                                      551  4-OCH.sub.3C.sub.6 H.sub.4CHCH                                                                           CH.sub.2 O                                      552  4-phenoxy-C.sub.6 H.sub.4CHCH                                                                            CH.sub.2 O                                      553  C.sub.6 H.sub.5(CH.sub.2).sub.3                                                                          CH.sub.2 O                                      554  C.sub.6 H.sub.5CH.sub.2 CH(CH.sub.3)CH.sub.2                                                             CH.sub.2 O                                      555  C.sub.6 H.sub.5(CH.sub.2).sub.4                                                                          CH.sub.2 O                                      556  C.sub.6 H.sub.5(CH.sub.2).sub.5                                                                          CH.sub.2 O                                      557  C.sub.6 H.sub.5(CH.sub.2).sub.6                                                                          CH.sub.2 O                                      558  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH(CH.sub.3)CH.sub.2                                          CH.sub.2 O                                      559  H                         OCH.sub.2                                       560  CH.sub.3                  OCH.sub.2                                       561  C.sub.2 H.sub.5           OCH.sub.2                                       562  n-C.sub.3 H.sub.7         OCH.sub.2                                       563  iso-C.sub.3 H.sub.7       OCH.sub.2                                       564  n-C.sub.4 H.sub.9         OCH.sub.2                                       565  (CH.sub.3).sub.2 CHCH.sub.2                                                                              OCH.sub.2                                       566  CH.sub.3 CH.sub.2 CH(CH.sub.3)                                                                           OCH.sub.2                                       567  tert.C.sub.4 H.sub.9      OCH.sub.2                                       568  CH.sub.3 CH.sub.2 C(CH.sub.3).sub.2                                                                      OCH.sub.2                                       569  (CH.sub.3).sub.3 CCH.sub.2                                                                               OCH.sub.2                                       570  (CH.sub.3).sub.2 CHCH.sub.2 CH.sub.2                                                                     OCH.sub.2                                       571  CH.sub.3 CH.sub.2 CH.sub.2 CH(C.sub.2 H.sub.5)                                                           OCH.sub.2                                       572  n-C.sub.5 H.sub.11        OCH.sub.2                                       573  n-C.sub.6 H.sub.13        OCH.sub.2                                       574  n-C.sub.7 H.sub.15        OCH.sub.2                                       575  n-C.sub.8 H.sub.17        OCH.sub.2                                       __________________________________________________________________________

    __________________________________________________________________________     576  n-C.sub.9 H.sub.19        OCH.sub.2                                       577  n-C.sub.10 H.sub.21       OCH.sub.2                                       578  n-C.sub.15 H.sub.31       OCH.sub.2                                       579  n-C.sub.17 H.sub.35       OCH.sub.2                                       580  CH.sub.2CH                OCH.sub.2                                       581  CH.sub.2C(CH.sub.3)       OCH.sub.2                                       582  CH.sub.3 CHCH             OCH.sub.2                                       583  CH.sub.3 CHC(CH.sub.3)    OCH.sub.2                                       584  (CH.sub.3).sub.2 CCH      OCH.sub.2                                       585  CH.sub.2CHCH.sub.2        OCH.sub.2                                       586  CH.sub.3 CHCHCH.sub.2     OCH.sub.2                                       587  (CH.sub.3).sub.2 CCHCH.sub.2                                                                             OCH.sub.2                                       588  CH.sub.3 CHCHCHCH         OCH.sub.2                                       589  (CH.sub.3).sub.2 CCHCH.sub.2 CH.sub.2 C(CH.sub.3)CH                                                      OCH.sub.2                                       590  (CH.sub.3).sub.2 CHCH.sub.2 CH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2                                       OCH.sub.2                                       591  (CH.sub.3).sub.2 CCHCH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2                                               OCH.sub.2                                       592  (CH.sub.3).sub.2 CCHCH.sub.2 CH.sub. 2 CH(CH.sub.3)CH.sub.2                                              OCH.sub.2                                       593  CH.sub.3 OCH.sub.2        OCH.sub.2                                       594  C.sub.2 H.sub.5 OCH.sub.2 OCH.sub.2                                       595  CH.sub.3 CH(OCH.sub.3)    OCH.sub.2                                       596  CNCH.sub.2                OCH.sub.2                                       597  cyclopropyl               OCH.sub.2                                       598  cyclobutyl                OCH.sub.2                                       599  cyclopentyl               OCH.sub.2                                       600  cyclohexyl                OCH.sub.2                                       601  1-methylcyclopropyl       OCH.sub.2                                       602  2,2-dichloro-1-methyl-cyclopropyl                                                                        OCH.sub.2                                       603  2,2-dichloro-3,3-dimethyl-cyclopropyl                                                                    OCH.sub.2                                       604  2,2,3,3-tetramethylcyclopropyl                                                                           OCH.sub.2                                       605  2-(2'-methyl-1'-propenyl-)-3,3-dimethylcyclopropyl                                                       OCH.sub.2                                       606  2-(2',2'-difluorovinyl)-3,3-dimethylcyclopropyl                                                          OCH.sub.2                                       607  2-(2',2'-dichlorovinyl)-3,3-dimethylcyclopropyl                                                          OCH.sub.2                                       608  2-(2',2'-dibromovinyl)-3,3-dimethylcyclopropyl                                                           OCH.sub.2                                       609  2-phenylcyclopropyl       OCH.sub.2                                       610  2-(4'-chlorophenyl)cyclopropyl                                                                           OCH.sub.2                                       611  2,2-dichloro-3-phenylcyclopropyl                                                                         OCH.sub.2                                       612  2-carbomethoxy-cyclopropyl                                                                               OCH.sub.2                                       613  Cl.sub.2 CH               OCH.sub.2                                       614  Cl.sub.2 CH               OCH.sub.2                                       615  Cl.sub.3 C                OCH.sub.2                                       616  BrCH.sub.2                OCH.sub.2                                       617  CF.sub.3                  OCH.sub.2                                       618  CH.sub.3 CH(Cl)           OCH.sub.2                                       619  C.sub. 6 H.sub.5 (phenyl) OCH.sub.2                                       620  2-CH.sub.3C.sub.6 H.sub.4 OCH.sub.2                                       621  3-CH.sub.3C.sub.6 H.sub.4 OCH.sub.2                                       622  4-CH.sub.3C.sub.6 H.sub.4 OCH.sub.2                                       623  2,3-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      OCH.sub.2                                       624  2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      OCH.sub.2                                       625  2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      OCH.sub.2                                       626  3,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      OCH.sub.2                                       627  3,5-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      OCH.sub.2                                       628  2,4,6-(CH.sub.3).sub.2C.sub.6 H.sub.2                                                                    OCH.sub.2                                       629  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4                                                                       OCH.sub.2                                       630  2-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                                         OCH.sub.2                                       631  4-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                                         OCH.sub.2                                       632  2-ClC.sub.6 H.sub.4       OCH.sub.2      oil; .sup.1 H-NMR                                                              (CDCl.sub.3):                                                                  δ = 3.75(3H),5.03(2H),                                                   2                                                                              5.83(2H),6.58(1H),6.90(1H),                                                    1                                                                              7.0-7.6(8H)                      633  3-Cl C.sub.6 H.sub.4      OCH.sub.2                                       634  4-ClC.sub.6 H.sub.4       OCH.sub.2                                       635  2,4-Cl.sub.2C.sub.6 H.sub.3                                                                              OCH.sub.2                                       636  2,5-Cl.sub.2C.sub.6 H.sub.3                                                                              OCH.sub.2                                       637  2,6-Cl.sub.2C.sub.6 H.sub.3                                                                              OCH.sub.2                                       638  3,4-Cl.sub.2C.sub.6 H.sub.3                                                                              OCH.sub.2                                       639  3,5-Cl.sub.2C.sub.6 H.sub.3                                                                              OCH.sub.2                                       640  2,4,5-Cl.sub.3C.sub.6 H.sub.2                                                                            OCH.sub.2                                       641  2,3,4,5,6-Cl.sub.5C.sub.6 OCH.sub.2                                       642  6-F,2-ClC.sub.6 H.sub.3   OCH.sub.2                                       643  2-FC.sub.6 H.sub.4        OCH.sub.2                                       644  3-FC.sub.6 H.sub.4        OCH.sub.2                                       645  4-FC.sub.6 H.sub.4        OCH.sub.2                                       646  2,4-F.sub.2C.sub.6 H.sub.3                                                                               OCH.sub.2                                       647  2,6-F.sub.2C.sub.6 H.sub.3                                                                               OCH.sub.2                                       648  2,3,4,5,6-F.sub.5C.sub.6  OCH.sub.2                                       649  2-BrC.sub.6 H.sub.4       OCH.sub.2      oil; .sup.1 H-NMR                                                              (CDCl.sub.3):                                                                  δ = 3.77(3H),5.03(2H),                                                   .                                                                              5.83(2H),6.60(1H),6.83(2H),                                                    7.1-7.7(6H)                      650  3-BrC.sub.6 H.sub.4       OCH.sub.2                                       651  4-BrC.sub.6 H.sub.4       OCH.sub.2                                       652  2-CF.sub.3C.sub.6 H.sub.4 OCH.sub.2                                       653  3-CF.sub.3C.sub.6 H.sub.4 OCH.sub.2                                       654  4-CF.sub.3C.sub.6 H.sub.4 OCH.sub.2                                       655  2-OCH.sub.3C.sub.6 H.sub.4                                                                               OCH.sub.2                                       656  3-OCH.sub.3C.sub.6 H.sub.4                                                                               OCH.sub.2                                       657  4-OCH.sub.3C.sub.6 H.sub.4                                                                               OCH.sub.2                                       658  3,4-(OCH.sub.3).sub.2C.sub.6 H.sub.3                                                                     OCH.sub.2                                       659  3,4,5-(OCH.sub.3).sub.3C.sub.6 H.sub.2                                                                   OCH.sub.2                                       660  4-t-C.sub.4 H.sub.9 OC.sub.6 H.sub.4                                                                     OCH.sub.2                                       661  2-phenoxy-C.sub.6 H.sub.4 OCH.sub.2                                       662  3-phenoxy-C.sub.6 H.sub.4 OCH.sub.2                                       663  4-phenoxy-C.sub.6 H.sub.4 OCH.sub.2                                       664  C.sub.6 H.sub.5CH.sub.2   OCH.sub.2                                       665  2-FC.sub.6 H.sub.4CH.sub.2                                                                               OCH.sub.2                                       666  3-FC.sub.6 H.sub.4CH.sub.2                                                                               OCH.sub.2                                       667  4-FC.sub.6 H.sub.4CH.sub.2                                                                               OCH.sub. 2                                      668  2-ClC.sub.6 H.sub.4CH.sub.2                                                                              OCH.sub.2                                       669  3-ClC.sub.6 H.sub.4CH.sub.2                                                                              OCH.sub.2                                       670  4-ClC.sub.6 H.sub.4CH.sub.2                                                                              OCH.sub.2                                       671  2-Cl,6FC.sub.6 H.sub.3CH.sub.2                                                                           OCH.sub.2                                       672  2,4-Cl.sub.2C.sub.6 H.sub.3CH.sub.2                                                                      OCH.sub.2                                       673  2,6-Cl.sub.2C.sub.6 H.sub.3CH.sub.2                                                                      OCH.sub.2                                       674  3,5-Cl.sub.2C.sub.6 H.sub.3CH.sub.2                                                                      OCH.sub.2                                       675  2,4,6-Cl.sub.3C.sub.6 H.sub.2CH.sub.2                                                                    OCH.sub.2                                       676  2-CH.sub.3C.sub.6 H.sub.4CH.sub.2                                                                        OCH.sub.2                                       677  3-CH.sub.3C.sub.6 H.sub.4CH.sub.2                                                                        OCH.sub.2                                       678  4-CH.sub.3C.sub.6 H.sub.4CH.sub.2                                                                        OCH.sub.2                                       679  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2                                                               OCH.sub.2                                       680  2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3CH.sub.2                                                              OCH.sub.2                                       681  2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3CH.sub.2                                                              OCH.sub.2                                       682  2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2CH.sub.2                                                            OCH.sub.2                                       683  2-OCH.sub.3C.sub.6 H.sub.4CH.sub.2                                                                       OCH.sub.2                                       684  3-OCH.sub.3C.sub.6 H.sub.4CH.sub.2                                                                       OCH.sub.2                                       685  4-OCH.sub.3C.sub.6 H.sub.4CH.sub.2                                                                       OCH.sub.2                                       686  2-CF.sub.3C.sub.6 H.sub.4CH.sub.2                                                                        OCH.sub.2                                       687  3-CF.sub.3C.sub.6 H.sub.4CH.sub.2                                                                        OCH.sub.2                                       688  4-CF.sub.3C.sub.6 H.sub.4CH.sub.2                                                                        OCH.sub.2                                       689  4-O-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2                                                             OCH.sub.2                                       690  4-OC.sub.6 H.sub.5C.sub.6 H.sub.4CH.sub.2                                                                OCH.sub.2                                       691  4-C.sub.6 H.sub.5CH.sub.2 OCH.sub.2                                       692  2-BrC.sub.6 H.sub.4CH.sub.2                                                                              OCH.sub.2                                       693  3-BrC.sub.6 H.sub.4CH.sub.2                                                                              OCH.sub.2                                       694  4-BrC.sub.6 H.sub.4CH.sub.2                                                                              OCH.sub.2                                       695  C.sub.6 H.sub.5CH(CH.sub.3)                                                                              OCH.sub.2                                       696  C.sub.6 H.sub.5CH(C.sub.2 H.sub.5)                                                                       OCH.sub.2                                       697  C.sub.6 H.sub.5CH(iso-C.sub.3 H.sub.)                                                                    OCH.sub.2                                       698  C.sub.6 H.sub.5CH.sub.2 CH.sub.2                                                                         OCH.sub.2                                       699  C.sub.6 H.sub.5CH.sub.2 CH(CH.sub.3)                                                                     OCH.sub.3                                       700  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH.sub.2                                                      OCH.sub.2                                       701  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH(CH.sub.3)                                                  OCH.sub.2                                       702  2-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.2                                                                     OCH.sub.2                                       703  3-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.2                                                                     OCH.sub.2                                       704  4-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.3                                                                     OCH.sub.2                                       705  C.sub.6 H.sub.5CHCH       OCH.sub.2                                       706  C.sub.6 H.sub.5(CH.sub.2).sub.3                                                                          OCH.sub.2                                       707  C.sub.6 H.sub.5CH.sub.2 CH(CH.sub.3)CH.sub.2                                                             OCH.sub.2                                       708  C.sub.6 H.sub.5(CH.sub.2).sub.4                                                                          OCH.sub.2                                       709  C.sub.6 H.sub.5(CH.sub.2).sub.5                                                                          OCH.sub.2                                       710  C.sub.6 H.sub.5(CH.sub.2).sub.6                                                                          OCH.sub.2                                       711  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH(CH.sub.3)CH.sub.2                                          OCH.sub.2                                       712  H                          COOCH.sub.2                                    713  CH.sub.3                  COOCH.sub.2                                     714  C.sub.2 H.sub.5           COOCH.sub.2                                     715  n-C.sub.3 H.sub.7         COOCH.sub.2                                     716  iso-C.sub.3 H.sub.7       COOCH.sub.2                                     717  n-C.sub.4 H.sub.9         COOCH.sub.2                                     718  (CH.sub.3).sub.2 CHCH.sub.2                                                                              COOCH.sub.2                                     719  CH.sub.3 CH.sub.2 CH(CH.sub.3)                                                                           COOCH.sub.2                                     720  tert.C.sub.4 H.sub.9      COOCH.sub.2    oil; IR (film): 1727,1480,                                                     1281,1150,771 cm.sup.-1          721  CH.sub.3 CH.sub.2 C(CH.sub.3).sub.2                                                                      COOCH.sub.2                                     722  (CH.sub.3).sub.3 CCH.sub.2                                                                               COOCH.sub.2                                     723  (CH.sub.3).sub.2 CHCH.sub.2 CH.sub.2                                                                     COOCH.sub.2                                     724  CH.sub.3 CH.sub.2 CH.sub.2 CH(C.sub.2 H.sub.5)                                                           COOCH.sub.2                                     725  n-C.sub.5 H.sub.11        COOCH.sub.2                                     726  n-C.sub.6 H.sub.13        COOCH.sub.2                                     727  n-C.sub.7 H.sub.15        COOCH.sub.2                                     728  n-C.sub.8 H.sub.17        COOCH.sub.2                                     729  n-C.sub.9 H.sub.19        COOCH.sub.2                                     730  n-C.sub.10 H.sub.21       COOCH.sub.2                                     731  n-C.sub.15 H.sub.31       COOCH.sub.2                                     732  n-C.sub.17 H.sub.35       COOCH.sub.2                                     733  CH.sub.2CH                COOCH.sub.2                                     734  CH.sub.2C(CH.sub.3)       COOCH.sub.2                                     735  CH.sub.3 CHCH             COOCH.sub.2                                     736  CH.sub.3 CHC(CH.sub.3)    COOCH.sub.2                                     737  (CH.sub.3).sub.2 CCH      COOCH.sub.2                                     738  CH.sub.2CHCH.sub.2        COOCH.sub.2                                     739  CH.sub.3 CHCHCH.sub.2     COOCH.sub.2                                     740  (CH.sub.3).sub.2 CCHCH.sub.2                                                                             COOCH.sub.2                                     741  CH.sub.3 CHCHCHCH         COOCH.sub.2                                     742  (CH.sub.3).sub.2 CCHCH.sub.2 CH.sub.2 C(CH.sub.3)CH                                                      COOCH.sub.2                                     743  (CH.sub.3).sub.2 CHCH.sub.2 CH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2                                       COOCH.sub.2                                     744  (CH.sub.3).sub.2 CCHCH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2                                               COOCH.sub.2                                     745  HC C                      COOCH.sub.2                                     746  C.sub.6 H.sub.5CC         COOCH.sub.2                                     747  CH.sub.3 OCH.sub.2        COOCH.sub.2                                     748  C.sub.2 H.sub.5 OCH.sub.2 COOCH.sub.2                                     749  CH.sub.3 CH(OCH.sub.3)    COOCH.sub.2                                     750  CNCH.sub.2                COOCH.sub.2                                     751  cyclopropyl               COOCH.sub.2    oil; IR (Film): 2958,1726,                                                     1399,1168,1082,772                                                             cm.sup.-1                        752  cyclobutyl                COOCH.sub.2                                     753  cyclopentyl               COOCH.sub.2                                     754  cyclohexyl                COOCH.sub.2                                     755  1-methylcyclopropyl       COOCH.sub.2    oil; IR (film):                                                                1724,1323,1214,1197,                                                           1157,771,75 cm.sup.-1            756  2,2-dichloro-1-methyl-cyclopropyl                                                                        COOCH.sub.2                                     757  2,2-dichloro-3,3-dimethyl-cyclopropyl                                                                    COOCH.sub.2                                     758  2,2,3,3-tetramethylcyclopropyl                                                                           COOCH.sub.2                                     759  2-(2'-methyl-1'-propenyl-)-3,3-dimethylcyclopropyl                                                       COOCH.sub.2                                     760  2-(2',2'-difluorovinyl)-3,3-dimethylcyclopropyl                                                          COOCH.sub.2                                     761  2-(2',2'-dichlorovinyl)-3,3-dimethylcyclopropyl                                                          COOCH.sub.2                                     762  2-(2',2'-dibromovinyl)-3,3-dimethylcyclopropyl                                                           COOCH.sub.2                                     763  2-phenylcyclopropyl        COOCH.sub.2                                    764  2-(4'-chlorophenyl)cyclopropyl                                                                           COOCH.sub.2                                     765  2,2-dichloro-3-phenylcyclopropyl                                                                         COOCH.sub.2                                     766  2-carbomethoxy-cyclopropyl                                                                               COOCH.sub.2                                     767  Cl.sub.2 CH               COOCH.sub.2                                     768  Cl.sub.2 CH               COOCH.sub.2                                     769  Cl.sub.3 C                COOCH.sub.2                                     770  BrCH.sub.2                COOCH.sub.2                                     771  CF.sub.3                  COOCH.sub.2                                     772  CH.sub.3 CH(Cl)           COOCH.sub.2                                     773  C.sub.6 H.sub.5 (phenyl)  COOCH.sub.2    oil; IR (film)                                                                 1722,1451,1314,1270                                                            1213,1110,713 cm.sup.-1          774  2-CH.sub.3C.sub.6 H.sub.4 COOCH.sub.2                                     775  3-CH.sub.3C.sub.6 H.sub.4 COOCH.sub.2                                     776  4-CH.sub.3C.sub.6 H.sub.4 COOCH.sub.2                                     777  2,3-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      COOCH.sub.2                                     778  2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      COOCH.sub.2                                     779  2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      COOCH.sub.2                                     780  3,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      COOCH.sub.2                                     781  3,5-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      COOCH.sub.2                                     782  2,4,6-(CH.sub.3).sub.2C.sub.6 H.sub.2                                                                    COOCH.sub.2                                     783  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4                                                                       COOCH.sub.2                                     784  2-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                                         COOCH.sub.2                                     785  4-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                                         COOCH.sub.2                                     786  2-ClC.sub.6 H.sub.4       COOCH.sub.2                                     787  3-ClC.sub.6 H.sub.4       COOCH.sub.2                                     788  4-ClC.sub.6 H.sub.4       COOCH.sub.2                                     789  2,4-Cl.sub.2C.sub.6 H.sub.3                                                                              COOCH.sub.2                                     790  2,5-Cl.sub.2C.sub.6 H.sub.3                                                                              COOCH.sub.2                                     791  2,6-Cl.sub.2C.sub.6 H.sub.3                                                                              COOCH.sub.2                                     792  3,4-Cl.sub.2C.sub.6 H.sub.3                                                                              COOCH.sub.2                                     793  3,5-Cl.sub.2C.sub.6 H.sub.3                                                                              COOCH.sub.2                                     794  2,4,5-Cl.sub.3C.sub.6 H.sub.3                                                                            COOCH.sub.2                                     795  2,3,4,5,6-Cl.sub.5C.sub.6 COOCH.sub.2                                     796  6-F,2-ClC.sub.6 H.sub.3   COOCH.sub.2                                     797  2-FC.sub.6 H.sub.4        COOCH.sub.2                                     798  3-FC.sub.6 H.sub.4        COOCH.sub.2                                     799  4-FC.sub.6 H.sub.4        COOCH.sub.2                                     800  2,4-F.sub.2C.sub.6 H.sub.3                                                                               COOCH.sub.2                                     801  2,6-F.sub.2C.sub.6 H.sub.3                                                                               COOCH.sub.2                                     802  2,3,4,5,6-F.sub.5C.sub.6  COOCH.sub.2                                     803  2-BrC.sub.6 H.sub.4       COOCH.sub.2                                     804  3-BrC.sub.6 H.sub.4       COOCH.sub.2                                     805  4-BrC.sub.6 H.sub.4       COOCH.sub.2                                     806  2-CF.sub.3C.sub.6 H.sub.4 COOCH.sub.2                                     807  3-CF.sub.3C.sub.6 H.sub.4 COOCH.sub.2                                     808  4-CF.sub.3C.sub.6 H.sub.4 COOCH.sub.2                                     809  2-OCH.sub.3C.sub.6 H.sub.4                                                                               COOCH.sub.2                                     810  3-OCH.sub.3C.sub.6 H.sub.4                                                                               COOCH.sub.2                                     811  4-OCH.sub.3C.sub.6 H.sub.4                                                                               COOCH.sub.2                                     812  3,4-(OCH.sub.3).sub.2C.sub.6 H.sub.3                                                                     COOCH.sub.2                                     813  3,4,5-(OCH.sub.3).sub.3C.sub.6 H.sub.3                                                                   COOCH.sub.2                                     814  4-t-C.sub.4 H.sub. 9 OC.sub.6 H.sub.4                                                                    COOCH.sub.2                                     815  2-phenoxy-C.sub.6 H.sub.4 COOCH.sub.2                                     816  3-phenoxy-C.sub.6 H.sub.4 COOCH.sub.2                                     817  4-phenoxy-C.sub.6 H.sub.4 COOCH.sub.2                                     818  C.sub.6 H.sub.5CH.sub.2   COOCH.sub.2                                     819  2-FC.sub.6 H.sub.4CH.sub.2                                                                               COOCH.sub.2                                     820  3-FC.sub.6 H.sub.4CH.sub.2                                                                               COOCH.sub.2                                     821  4-FC.sub.6 H.sub.4CH.sub.2                                                                               COOCH.sub.2                                     822  2-ClC.sub.6 H.sub.4CH.sub.2                                                                              COOCH.sub.2                                     823  3-ClC.sub.6 H.sub.4CH.sub.2                                                                              COOCH.sub.2                                     824  4-ClC.sub.6 H.sub.4CH.sub.2                                                                              COOCH.sub.2                                     825  2-Cl,6FC.sub.6 H.sub.3CH.sub.2                                                                           COOCH.sub.2                                     826  2,4-Cl.sub.2C.sub.6 H.sub.3CH.sub.2                                                                      COOCH.sub.2                                     827  2,6-Cl.sub.2C.sub.6 H.sub.3CH.sub.2                                                                      COOCH.sub.2                                     828  3,5-Cl.sub.2C.sub.6 H.sub.3CH.sub.2                                                                      COOCH.sub.2                                     829  2,4,6-Cl.sub.3C.sub.6 H.sub.2CH.sub.2                                                                    COOCH.sub.2                                     830  2-CH.sub.3C.sub.6 H.sub.4CH.sub.2                                                                        COOCH.sub.2                                     831  3-CH.sub.3C.sub.6 H.sub.4CH.sub.2                                                                        COOCH.sub.2                                     832  4-CH.sub.3C.sub.6 H.sub.4CH.sub.2                                                                        COOCH.sub.2                                     833  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2                                                               COOCH.sub.2                                     834  2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3CH.sub.2                                                              COOCH.sub.2                                     835  2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3CH.sub.2                                                              COOCH.sub.2                                     836  2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2CH.sub.2                                                            COOCH.sub.2                                     837  2-OCH.sub.3C.sub.6 H.sub.4CH.sub.2                                                                       COOCH.sub.2                                     838  3-OCH.sub.3C.sub.6 H.sub.4CH.sub.2                                                                       COOCH.sub.2                                     839  4-OCH.sub.3C.sub.6 H.sub.4CH.sub.2                                                                       COOCH.sub.2                                     840  2-CF.sub.3C.sub.6 H.sub.4CH.sub.2                                                                        COOCH.sub.2                                     841  3-CF.sub.3C.sub.6 H.sub.4CH.sub.2                                                                        COOCH.sub.2                                     842  4-CF.sub.3C.sub.6 H.sub.4CH.sub.2                                                                        COOCH.sub.2                                     843  4-O-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub. 2                                                            COOCH.sub.2                                     844  4-OC.sub.6 H.sub.5C.sub.6 H.sub.4CH.sub.2                                                                COOCH.sub.2                                     845  4-C.sub.6 H.sub.5C.sub.6 H.sub.4CH.sub.2                                                                 COOCH.sub.2                                     846  2-BrC.sub.6 H.sub.4CH.sub.2                                                                              COOCH.sub.2                                     847  3-BrC.sub.6 H.sub.4CH.sub.2                                                                              COOCH.sub.2                                     848  4-BrC.sub.6 H.sub.4CH.sub.2                                                                              COOCH.sub.2                                     849  C.sub.6 H.sub.5CH(CH.sub.3)                                                                              COOCH.sub.2                                     850  C.sub.6 H.sub.5CH(C.sub.2 H.sub.5)                                                                       COOCH.sub.2                                     851  C.sub.6 H.sub.5CH(iso-C.sub.3 H.sub.7)                                                                   COOCH.sub.2                                     852  C.sub.6 H.sub.5CH(OH)     COOCH.sub.2                                     853  2-OCH.sub.3C.sub.6 H.sub.4CH(OH)                                                                         COOCH.sub.2                                     854  4-OCH.sub.3C.sub.6 H.sub.4CH(OH)                                                                         COOCH.sub.2                                     855  3,4-(OCH.sub.3).sub.2C.sub.6 H.sub.3CH(OH)                                                               COOCH.sub.2                                     856  2-OCH.sub.3C.sub.6 H.sub.4CH(OCH.sub.3)                                                                  COOCH.sub.2                                     857  4-OCH.sub.3C.sub.6 H.sub.4CH(OCH.sub.3)                                                                  COOCH.sub. 2                                    858  3,4-(OCH.sub.3).sub.2C.sub.6 H.sub.3CH(OCH.sub.3)                                                        COOCH.sub.2                                     859  C.sub.6 H.sub.5CH.sub.2 CH.sub.2                                                                         COOCH.sub.2                                     860  C.sub.6 H.sub.5CH.sub.2 CH(CH.sub.3)                                                                     COOCH.sub.2                                     861  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH.sub.2                                                      COOCH.sub.2                                     862  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2 CH(CH.sub.3)                                                  COOCH.sub.2                                     863  2-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.2                                                                     COOCH.sub.2                                     864  3-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.2                                                                     COOCH.sub.2                                     865  4-ClC.sub.6 H.sub.4CH.sub.2 CH.sub.3                                                                     COOCH.sub.2                                     866  C.sub.6 H.sub.5CHCH       COOCH.sub.2    oil; IR (film)                                                                 1719,1637,1311,1204                                                            1164,768 cm.sup.-1               867  2-ClC.sub.6 H.sub.4CHCH   COOCH.sub.2                                     868  3-ClC.sub.6 H.sub.4CHCH   COOCH.sub.2                                     869  4-ClC.sub.6 H.sub.4CHCH   COOCH.sub.2                                     870  2,4-Cl.sub. 2C.sub.6 H.sub.3CHCH                                                                         COOCH.sub.2                                     871  2-FC.sub.6 H.sub.4CHCH    COOCH.sub.2                                     872  4-FC.sub.6 H.sub.4CHCH    COOCH.sub.2                                     873  2-CH.sub.3C.sub.6 H.sub.4CHCH                                                                            COOCH.sub.2                                     874  4-CH.sub.3C.sub.6 H.sub.4CHCH                                                                            COOCH.sub.2                                     875  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CHCH                                                                   COOCH.sub.2                                     876  2-OCH.sub.3C.sub.6 H.sub.4CHCH                                                                           COOCH.sub.2                                     877  4-OCH.sub.3C.sub.6 H.sub.4CHCH                                                                           COOCH.sub.2                                     878  4-Phenoxy-C.sub.6 H.sub.4CHCH                                                                            COOCH.sub.2                                     879  C.sub.6 H.sub.5(CH.sub.2).sub.3                                                                          COOCH.sub.2                                     880  C.sub.6 H.sub.5CH.sub.2 CH(CH.sub.3)CH.sub.2                                                             COOCH.sub.2                                     881  C.sub.6 H.sub.5(CH.sub.2).sub.4                                                                          COOCH.sub.2                                     882  C.sub.6 H.sub.5(CH.sub.2).sub.5                                                                          COOCH.sub.2                                     883  C.sub.6 H.sub.5(CH.sub.2).sub.6                                                                          COOCH.sub.2                                     884  4-t-C.sub.4 H.sub.9C.sub. 6 H.sub.4CH.sub.2 CH(CH.sub.3)CH.sub.2                                         COOCH.sub.2                                     885  C.sub.6 H.sub.5           CC                                              886  2-ClC.sub.6 H.sub.4       CC                                              887  3-ClC.sub.6 H.sub.4       CC                                              888  4-ClC.sub.6 H.sub.4       CC                                              889  C.sub.6 H.sub.5 OCH.sub.2 CC                                              890  2-ClC.sub.6 H.sub.5 OCH.sub.2                                                                            CC                                              891  3-ClC.sub.6 H.sub.5 OCH.sub.2                                                                            CC                                              892  4-ClC.sub.6 H.sub.5 OCH.sub.2                                                                            CC                                              893  CH.sub.3 OOC              CC                                              894  t-C.sub.4 H.sub.9 OOC     C C                                             895  C.sub.6 H.sub.6           CH.sub.2                                        896  2-FC.sub.6 H.sub.4        CH.sub.2                                        897  3-FC.sub.6 H.sub.4        CH.sub.2                                        898  4-FC.sub.6 H.sub.4        CH.sub.2                                        899  2-ClC.sub.6 H.sub.4       CH.sub.2                                        900  3-ClC.sub.6 H.sub.4       CH.sub.2                                        901  4-ClC.sub.6 H.sub.4       CH.sub.2                                        902  2Cl,6FC.sub.6 H.sub.3     CH.sub.2                                        903  2,4-Cl.sub.2C.sub.6 H.sub.3                                                                              CH.sub.2                                        904  2,6-Cl.sub.2C.sub.6 H.sub.3                                                                              CH.sub.2                                        905  3,5-Cl.sub.2C.sub.6 H.sub.3                                                                              CH.sub.2                                        906  2,4,6-Cl.sub.3C.sub.6 H.sub.2                                                                            CH.sub.2                                        907  2-CH.sub.3C.sub.6 H.sub.4 CH.sub.2                                        908  3-CH.sub.3C.sub.6 H.sub.4 CH.sub.2                                        909  4-CH.sub.3C.sub.6 H.sub.4 CH.sub.2                                        910  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4                                                                       CH.sub.2                                        911  2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      CH.sub.2                                        912  2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                       CH.sub.2                                       913  2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2                                                                    CH.sub.2                                        914  2-OCH.sub.3C.sub.6 H.sub.4                                                                               CH.sub.2                                        915  3-OCH.sub.3C.sub.6 H.sub.4                                                                               CH.sub.2                                        916  4-OCH.sub.3C.sub.6 H.sub.4                                                                               CH.sub.2                                        917  2-CF.sub.3C.sub.6 H.sub.4 CH.sub.2                                        918  3-CF.sub.3C.sub.6 H.sub.4 CH.sub.2                                        919  4-CF.sub.3C.sub.6 H.sub.4 CH.sub.2                                        920  4-O-t-C.sub.4 H.sub.9C.sub.6 H.sub.4                                                                     CH.sub.2                                        921  4-OC.sub.6 H.sub.5C.sub.6 H.sub.4                                                                        CH.sub.2                                        922  4-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                                         CH.sub.2                                        923  2-BrC.sub.6 H.sub.4       CH.sub.2                                        924  4-BrC.sub.6 H.sub.4       CH.sub.2                                         925  Br                        CH.sub.2                                                                                     v. specification for data        926  Br.sup.- (C.sub.6 H.sub.5).sub.3 P.sup.+                                                                 CH.sub.2                                        927  Cl.sup.- (C.sub.6 H.sub.5).sub.3 P.sup.+                                                                 CH.sub.2                                        928  Br.sub.2                                                                                                  ##STR6##                                       929  Cl.sub.2                                                                                                  ##STR7##                                       930  OCH                       --                                              931  iso-C.sub.3 H.sub.7       O                                               932  CH.sub.3 CH.sub.2 CH(CH.sub.3)                                                                           O                                               933  ter.C.sub.4 H.sub.9       O                                               934  CH.sub.3 CH.sub.2 C(CH.sub.3).sub.2                                                                      O                                               935  CH.sub.3 CH.sub.2 CH.sub.2 CH(C.sub.2 H.sub.5)                                                           O                                               936  CH.sub.2CHCH.sub.2        O                                               937  CH.sub.3 CHCHCH.sub.2     O                                               938  (CH.sub.3).sub.2 CCHCH.sub.2                                                                             O                                               939  CH.sub.3 OCH.sub.2        O                                               940  CNCH.sub.2                O                                               941  cyclopropyl               O                                               942  cyclobutyl                O                                               943  cyclopentyl               O                                               944  cyclohexyl                O                                               945  1-methylcyclohexyl        O                                               946  1-methylcyclopropyl       O                                               947  Cl.sub.3 C                O                                               948  CF.sub.3 C                O                                               949  C.sub.6 H.sub.5 (phenyl)  O                                               950  2-CH.sub.3C.sub.6 H.sub.4 O                                               951  3-CH.sub.3C.sub.6 H.sub.4 O                                               952  4-CH.sub.3C.sub.6 H.sub.4 O                                               953  2,3-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      O                                               954  2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      O                                               955  2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      O                                               956  3,4-(CH.sub. 3).sub.2C.sub.6 H.sub.3                                                                     O                                               957  3,5-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      O                                               958  2,4,6-(CH.sub.3).sub.2C.sub.6 H.sub.2                                                                    O                                               959  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4                                                                       O                                               960  2-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                                         O                                               961  4-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                                         O                                               962  2-ClC.sub.6 H.sub.4       O                                               963  3-ClC.sub.6 H.sub.4       O                                               964  4-ClC.sub.6 H.sub.4       O                                               965  2,4-Cl.sub.2C.sub.6 H.sub.3                                                                              O                                               966  2,5-Cl.sub.2C.sub.6 H.sub.3                                                                              O                                               967  2,6-Cl.sub.2C.sub.6 H.sub.3                                                                              O                                               968  3,4-Cl.sub.2C.sub.6 H.sub.3                                                                              O                                               969  3,5-Cl.sub.2C.sub.6 H.sub.3                                                                              O                                               970  2,4,5-Cl.sub.3C.sub.6 H.sub.2                                                                            O                                               971  2,3,4,5,6-Cl.sub.5C.sub.6 O                                               972  6-F,2-ClC.sub.6 H.sub.3   O                                               973  2-FC.sub.6 H.sub.4        O                                               974  3-FC.sub.6 H.sub.4        O                                               975  4-FC.sub.6 H.sub.4        O                                               976  2,4-F.sub.2C.sub.6 H.sub.3                                                                               O                                               977  2,6-F.sub.2C.sub.6 H.sub.3                                                                               O                                               978  2,3,4,5,6-F.sub.5C.sub.6  O                                               979  2-BrC.sub.6 H.sub.4       O                                               980  3-BrC.sub.6 H.sub.4       O                                               981  4-BrC.sub. 6 H.sub.4      O                                               982  2-CF.sub.3C.sub.6 H.sub.4 O                                               983  3-CF.sub.3C.sub.6 H.sub.4 O                                               984  4-CF.sub.3C.sub.6 H.sub.4 O                                               985  2-OCH.sub.3C.sub.6 H.sub.4                                                                               O                                               986  3-OCH.sub.3C.sub.6 H.sub.4                                                                               O                                               987  4-OCH.sub.3C.sub.6 H.sub.4                                                                               O                                               988  3,4-(OCH.sub.3).sub.2C.sub.6 H.sub.3                                                                     O                                               989  3,4,5-(OCH.sub.3).sub.3C.sub.6 H.sub.2                                                                   O                                               990  4-t-C.sub.4 H.sub.9 OC.sub.6 H.sub.4                                                                     O                                               991  2-phenoxy-C.sub.6 H.sub.4 O                                               992  3-phenoxy-C.sub.6 H.sub.4 O                                               993  4-phenoxy-C.sub.6 H.sub.4 O                                               994  C.sub.6 H.sub.5           SCH.sub.2                                       995  2-FC.sub.6 H.sub.4        SCH.sub.2                                       996  3-FC.sub.6 H.sub.4        SCH.sub.2                                       997  4-FC.sub.6 H.sub.4        SCH.sub.2                                       998  2-ClC.sub.6 H.sub.4       SCH.sub.2                                       999  3-ClC.sub.6 H.sub.4       SCH.sub.2                                       1000 4-ClC.sub.6 H.sub.4       SCH.sub.2                                       1001 2Cl,6FC.sub.6 H.sub.3     SCH.sub.2                                       1002 2,4-Cl.sub.2C.sub.6 H.sub.3                                                                              SCH.sub.2                                       1003 2,6-Cl.sub.2C.sub.6 H.sub.3                                                                              SCH.sub. 2                                      1004 3,5-Cl.sub.2C.sub.6 H.sub.3                                                                              SCH.sub.2                                       1005 2,4,6-Cl.sub.3C.sub.6 H.sub.2                                                                            SCH.sub.2                                       1006 2-CH.sub.3C.sub.6 H.sub.4 SCH.sub.2                                       1007 3-CH.sub.3C.sub.6 H.sub.4 SCH.sub.2                                       1008 4-CH.sub.3C.sub.6 H.sub.4 SCH.sub.2                                       1009 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4                                                                       SCH.sub.2                                       1010 2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      SCH.sub.2                                       1011 2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                                      SCH.sub.2                                       1012 2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2                                                                    SCH.sub.2                                       1013 2-OCH.sub.3C.sub.6 H.sub.4                                                                               SCH.sub.2                                       1014 3-OCH.sub.3C.sub.6 H.sub.4                                                                               SCH.sub.2                                       1015 4-OCH.sub.3C.sub.6 H.sub.4                                                                               SCH.sub.2                                       1016 2-CF.sub.3C.sub.6 H.sub.4 SCH.sub.2                                       1017 3-CF.sub.3C.sub.6 H.sub.4 SCH.sub.2                                       1018 4-CF.sub.3C.sub.6 H.sub.4 SCH.sub.3                                       1019 4-O-t-C.sub.4 H.sub.9C.sub.6 H.sub.4                                                                     SCH.sub.2                                       1020 4-O-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                                       SCH.sub.2                                       1021 4-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                                         SCH.sub.2                                       1022 2-BrC.sub.6 H.sub.4       SCH.sub.2                                       1023 4-BrC.sub.6 H.sub.4       SCH.sub.2                                       1024 C.sub.6 H.sub.5           S                                               1025 2-ClC.sub.6 H.sub.4       S                                               1026 3-ClC.sub.6 H.sub.4       S                                               1027 4-ClC.sub.6 H.sub.4       S                                               1028 2-CH.sub.3C.sub.6 H.sub.4 S                                               1029 4-CH.sub.3C.sub.6 H.sub.4 S                                               1030 4-C.sub.6 H.sub.5C.sub.6 H.sub.5                                                                         S                                               1031 CH.sub.3                  S                                               1032 C.sub.6 H.sub.5 O         CH.sub.2 CH.sub.2 O                             1033 2-ClC.sub.6 H.sub.4 O     CH.sub.2 CH.sub.2 O                             1034 3-ClC.sub.6 H.sub.4 O     CH.sub.2 CH.sub.2 O                             1035 4-ClC.sub.6 H.sub.4 O     CH.sub.2 CH.sub.2 O                             1036 2-CH.sub.3C.sub.6 H.sub.4 O                                                                              CH.sub.2 CH.sub.2 O                             1037 4-CH.sub.3C.sub.6 H.sub.4 O                                                                              CH.sub.2 CH.sub.2 O                             1038 2-OCH.sub.3C.sub.6 H.sub.4 O                                                                             CH.sub.2 CH.sub.2 O                             1039 4-OCH.sub.3C.sub.6 H.sub.4 O                                                                             CH.sub.2 CH.sub.2 O                             1040 2-CF.sub.3C.sub.6 H.sub.4 O                                                                              CH.sub.2 CH.sub.2 O                             1041 4-CF.sub.3C.sub.6 H.sub.4 O                                                                              CH.sub.2 CH.sub.2 O                             1042 C.sub.6 H.sub.5 OCH.sub.2 CH.sub.2 CH.sub.2 O                             1043 2-ClC.sub.6 H.sub.4 OCH.sub.2                                                                            CH.sub.2 CH.sub.2 O                             1044 4-ClC.sub.6 H.sub.4 OCH.sub.2                                                                            CH.sub.2 CH.sub.2 O                             1045 2-CH.sub.3C.sub.6 H.sub.4 OCH.sub.2                                                                      CH.sub.2 CH.sub.2 O                             1046 4-CH.sub.3C.sub.6 H.sub.4 OCH.sub.2                                                                      CH.sub.2 CH.sub.2 O                             1047 2-OCH.sub.3C.sub.6 H.sub.4 OCH.sub.2                                                                     CH.sub.2 CH.sub.2 O                             1048 4-OCH.sub.3C.sub.6 H.sub.4 OCH.sub.2                                                                     CH.sub.2 CH.sub.2 O                             1049 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4 OCH.sub.2                                                             CH.sub.2 CH.sub.2 O                             1050 C.sub.6 H.sub.5 OCH.sub.2 CH.sub.2                                                                       CH.sub.2 CH.sub.2 O                             1051 2-ClC.sub.6 H.sub.4 OCH.sub.2 CH.sub.2                                                                   CH.sub.2 CH.sub.2 O                             1052 4-ClC.sub.6 H.sub.4 OCH.sub.2 CH.sub.2                                                                   CH.sub.2 CH.sub.2 O                             1053 4-FC.sub.6 H.sub.4 OCH.sub.2 CH.sub.2                                                                    CH.sub.2 CH.sub.2 O                             1054 2-CH.sub.2C.sub.6 H.sub.4 OCH.sub.2 CH.sub.2                                                             CH.sub.2 CH.sub.2 O                             1055 4-CH.sub.3C.sub.6 H.sub.4 OCH.sub.2 CH.sub.2                                                             CH.sub.2 CH.sub.2 O                             1056 2-OCH.sub.3C.sub.6 H.sub.4 OCH.sub.2 CH.sub.2                                                            CH.sub.2 CH.sub.2 O                             1057 4-OCH.sub.3C.sub.6 H.sub.4 OCH.sub.2 CH.sub.2                                                            CH.sub.2 CH.sub.2 O                             1058 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4OCH.sub.2 CH.sub.2                                                     CH.sub.2 CH.sub.2 O                             1059 C.sub.6 H.sub.5 O(CH.sub.2).sub.3                                                                        CH.sub.2 CH.sub.2 O                             1060 2-ClC.sub.6 H.sub.4 O(CH.sub.2).sub.3                                                                    CH.sub.2 CH.sub.2 O                             1061 4-ClC.sub.6 H.sub.4 O(CH.sub.2).sub.3                                                                    CH.sub.2 CH.sub.2 O                             1062 C.sub.6 H.sub.5 O(CH.sub.2).sub.4                                                                        CH.sub.2 CH.sub.2 O                             1063 2-ClC.sub.6 H.sub.4O(CH.sub.2).sub.4                                                                     CH.sub.2 CH.sub.2 O                             1064 4-ClC.sub.6 H.sub.4 O(CH.sub.2).sub.4                                                                    CH.sub.2 CH.sub.2 O                             1065 C.sub.6 H.sub.5 O(CH.sub.2).sub.5                                                                        CH.sub.2 CH.sub.2 O                             1066 2-ClC.sub.6 H.sub.4 O(CH.sub.2).sub.5                                                                    CH.sub.2 CH.sub.2 O                             1067 4-ClC.sub.6 H.sub.4 O(CH.sub.2).sub.5                                                                    CH.sub.2 CH.sub.2 O                             1068 C.sub.6 H.sub.5 O(CH.sub.2).sub.6                                                                        CH.sub.2 CH.sub.2 O                             1069 C.sub.6 H.sub.5 OCH.sub.2 CH.sub.2 O                                                                     CH.sub.2 CH.sub.2 O                             1070 C.sub.6 H.sub.5           COO                                             1071 2-ClC.sub.6 H.sub.4       COO                                             1072 3-ClC.sub.6 H.sub.4       COO                                             1073 4-ClC.sub.6 H.sub.4       COO                                             1074 2-CH.sub.3C.sub.6 H.sub.4 COO                                             1075 4-CH.sub.3C.sub.6 H.sub.4 COO                                             1076 4-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                                         COO                                             1077 C.sub.6 H.sub.5           CO O                                            1078 2-ClC.sub.6 H.sub.4       COO                                             1079 3-ClC.sub.6 H.sub.4       COO                                             1080 4-ClC.sub.6 H.sub.4       COO                                             1081 2-CH.sub.3C.sub.6 H.sub.4 COO                                             1082 CH.sub.3                  COO                                             1083 t-C.sub.4 H.sub.9         COO                                             1084 CH.sub.2 C.sub.6 H.sub.5  COO                                             1085 C.sub.6 H.sub.5           HNCOO                                           1086 2-ClC.sub.6 H.sub.4       HNCOO                                           1087 4-ClC.sub.6 H.sub.4       HNCOO                                           1088 C.sub.6 H.sub.11          HNCOO                                           1089 n-C.sub.4 H.sub.9         HNCOO                                           1090 2-furyl                   CHCH                                            1091 5-nitro-2-furyl           CHCH                                            1092 5-chloro-2-furyl          CHCH                                            1093 2-(2'-furyl)-ethenyl      CHCH                                            1094 2-(5'-nitro-2'-furyl)ethenyl                                                                             CHCH                                            1095 3-furyl                   CHCH                                            1096 5-nitro-3-furyl           CHCH                                            1097 5-chloro-3-furyl          CHCH                                            1098 2-(3'-furyl)ethenyl       CHCH                                            1099 2-(5'-nitro-3'-furyl)ethenyl                                                                             CHCH                                            1100 benzofuran-2-yl           CHCH                                            1101 benzofuran-3-yl           CHCH                                            1102 2-thienyl                 CHCH                                            1103 5-nitro-2-thienyl         CHCH                                            1104 5-chloro-2-thienyl        CHCH                                            1105 2-(2'-thienyl)ethenyl     CHCH                                            1106 2-(5'-nitro-2'-thienyl)ethenyl                                                                           CHCH                                            1107 3-thienyl                 CHCH                                            1108 5-nitro-3-thienyl         CHCH                                            1109 5-chloro-3-thienyl        CHCH                                            1110 2-(3'-thienyl)ethenyl     CHCH                                            1111 2-(5'-nitro-3'-thienyl)ethenyl                                                                           CHCH                                            1112 benzothien-2-yl           CHCH                                            1113 benzothien-3-yl           CHCH                                            1114 N-methyl-pyrrol-2-yl      CHCH                                            1115 N-methyl-pyrrol-3-yl      CHCH                                            1116 N-methyl-pyrazol-3-yl     CHCH                                            1117 N-methyl-pyrazol-4-yl     CHCH                                            1118 N-methyl-pyrazol-5-yl     CHCH                                            1119 N-methyl-imidazol-2-yl    CHCH                                            1120 N-methyl-imidazol-4-yl    CHCH                                            1121 N-methyl-imidazol-5-yl    CHCH                                            1122 1-methyl-1,2,3-triazol-4-yl                                                                              CHCH                                            1123 1-methyl-1,2,3-triazol-5-yl                                                                              CHCH                                            1124 1-methyl-1,2,4-triazol-3-yl                                                                              CHCH                                            1125 1-methyl-1,2,4-triazol-5-yl                                                                              CHCH                                            1126 1-methyl-tetrazol-5-yl    CHCH                                            1127 isoxazol-3-yl             CHCH                                            1128 isoxazol-4-yl             CHCH                                            1129 isoxazol-5-yl             CHCH                                            1130 benisoxazol-3-yl          CHCH                                            1131 benzoxazol-2-yl           CHCH                                            1132 oxazol-2-yl               CHCH                                            1133 oxazol-4-yl               CHCH                                            1134 oxazol-5-yl               CHCH                                            1135 thiazol-2-yl              CHCH                                            1136 thiazol-4-yl              CHCH                                            1137 thiazol-5-yl              CHCH                                            1138 benzthiazol-2-yl          CHCH                                            1139 benzisothiazol-3-yl       CHCH                                            1140 isothiazol-3-yl           CHCH                                            1141 isothiazol-4-yl           CHCH                                            1142 isothiazol-5-yl           CHCH                                            1143 1,2,3-thiadiazol-4-yl     CHCH                                            __________________________________________________________________________

    __________________________________________________________________________     1144 1,2,4-thiadiazol-5-yl     CHCH                                            1145 1,3,4-thiadiazol-3-yl     CHCH                                            1146 2-furyl                   CH.sub.2 CH.sub.2                               1147 5-nitro-2-furyl           CH.sub.2 CH.sub.2                               1148 5-chloro-2-furyl          CH.sub.2 CH.sub.2                               1149 2-(2'-furyl)-ethenyl      CH.sub.2 CH.sub.2                               1150 2-(5'-nitro-2'-furyl)ethenyl                                                                             CH.sub.2 CH.sub.2                               1151 3-furyl                   CH.sub.2 CH.sub.2                               1152 5-nitro-3-furyl           CH.sub.2 CH.sub.2                               1153 5-chloro-3-furyl          CH.sub.2 CH.sub.2                               1154 2-(3'-furyl)ethenyl       CH.sub.2 CH.sub.2                               1155 2-(5'-nitro-3'-furyl)ethenyl                                                                             CH.sub.2 CH.sub.2                               1156 benzofuran-2-yl           CH.sub.2 CH.sub.2                               1157 benzofuran-3-yl           CH.sub.2 CH.sub.2                               1158 2-thienyl                 CH.sub.2 CH.sub.2                               1159 5-nitro-2-thienyl         CH.sub.2 CH.sub.2                               1160 5-chloro-2-thienyl        CH.sub.2 CH.sub.2                               1161 2-(2'-thienyl)ethenyl     CH.sub.2 CH.sub.2                               1162 2-(5'-nitro-2'-thienyl)ethenyl                                                                           CH.sub.2 CH.sub.2                               1163 3-thienyl                 CH.sub.2 CH.sub.2                               1164 5-nitro-3-thienyl         CH.sub.2 CH.sub.2                               1165 5-chloro-3-thienyl        CH.sub.2 CH.sub.2                               1166 2-(3'-thienyl)ethenyl     CH.sub.2 CH.sub.2                               1167 2-(5'-nitro-3'-thienyl)ethenyl                                                                           CH.sub.2 CH.sub.2                               1168 benzothien-2-yl           CH.sub.2 CH.sub.2                               1169 benzothien-3-yl           CH.sub.2 CH.sub.2                               1170 N-methyl-pyrrol-2-yl      CH.sub.2 CH.sub.2                               1171 N-methyl-pyrrol-3-yl      CH.sub.2 CH.sub.2                               1172 N-methyl-pyrazol-3-yl     CH.sub.2 CH.sub.2                               1173 N-methyl-pyrazol-4-yl     CH.sub.2 CH.sub.2                               1174 N-methyl-pyrazol-5-yl     CH.sub.2 CH.sub.2                               1175 N-methyl-imidazol-2-yl    CH.sub.2 CH.sub.2                               1176 N-methyl-imidazol-4-yl    CH.sub.2 CH.sub.2                               1177 N-methyl-imidazol-5-yl    CH.sub.2 CH.sub.2                               1178 1-methyl-1,2,3-triazol-4-yl                                                                              CH.sub.2 CH.sub.2                               1179 1-methyl-1,2,3-triazol-5-yl                                                                              CH.sub.2 CH.sub.2                               1180 1-methyl-1,2,4-triazol-3-yl                                                                              CH.sub.2 CH.sub.2                               1181 1-methyl-1,2,4-triazol-5-yl                                                                              CH.sub.2 CH.sub.2                               1182 1-methyl-tetrazol-5-yl    CH.sub.2 CH.sub.2                               1183 isoxazol-3-yl             CH.sub.2 CH.sub.2                               1184 isoxazol-4-yl             CH.sub.2 CH.sub.2                               1185 isoxazol-5-yl             CH.sub.2 CH.sub.2                               1186 benzisoxazol-3-yl         CH.sub.2 CH.sub.2                               1187 benzoxazol-2-yl           CH.sub.2 CH.sub.2                               1188 oxazol-2-yl               CH.sub.2 CH.sub.2                               1189 oxazol-4-yl               CH.sub.2 CH.sub.2                               1190 oxazol-5-yl               CH.sub.2 CH.sub.2                               1191 thiazol-2-yl              CH.sub.2 CH.sub.2                               1192 thiazol-4-yl              CH.sub.2 CH.sub.2                               1193 thiazol-5-yl              CH.sub.2 CH.sub.2                               1194 benzthiazol-2-yl          CH.sub.2 CH.sub.2                               1195 benzisothiazol-3-yl       CH.sub.2 CH.sub.2                               1196 isothiazol-3-yl           CH.sub.2 CH.sub.2                               1197 isothiazol-4-yl           CH.sub.2 CH.sub.2                               1198 isothiazol-5-yl           CH.sub.2 CH.sub.2                               1199 1,2,3-thiadiazol-4-yl     CH.sub.2 CH.sub.2                               1200 1,2,4-thiadiazol-5-yl     CH.sub.2 CH.sub.2                               1201 1,3,4-thiadiazol-3-yl     CH.sub.2 CH.sub.2                               1202 2-furyl                   CH.sub.2 O                                      1203 5-nitro-2-furyl           CH.sub.2 O                                      1204 5-chloro-2-furyl          CH.sub.2 O                                      1205 2-(2'-furyl)-ethenyl      CH.sub.2 O                                      1206 2-(5'-nitro-2'-furyl)ethenyl                                                                             CH.sub.2 O                                      1207 3-furyl                   CH.sub.2 O                                      1208 5-nitro-3-furyl           CH.sub.2 O                                      1209 5-chloro-3-furyl          CH.sub.2 O                                      1210 2-(3'-furyl)ethenyl       CH.sub.2 O                                      1211 2-(5'-nitro-3'-furanyl)ethenyl                                                                           CH.sub.2 O                                      1212 benzofuran-2-yl           CH.sub.2 O                                      1213 benzofuran-3-yl           CH.sub.2 O                                      1214 2-thienyl                 CH.sub.2 O                                      1215 5-nitro-2-thienyl         CH.sub.2 O                                      1216 5-chloro-2-thienyl        CH.sub.2 O                                      1217 2-(2'-thienyl)ethenyl     CH.sub.2 O                                      1218 2-(5'-nitro-2'-thienyl)ethenyl                                                                           CH.sub.2 O                                      1219 3-thienyl                 CH.sub.2 O                                      1220 5-nitro-3-thienyl         CH.sub.2 O                                      1221 5-chloro-3-thienyl        CH.sub.2 O                                      1222 2-(3'-thienyl)ethenyl     CH.sub.2 O                                      1223 2-(5'-nitro-3'-thienyl)ethenyl                                                                           CH.sub.2 O                                      1224 benzothien-2-yl           CH.sub.2 O                                      1225 benzothien-3-yl           CH.sub.2 O                                      1226 N-methyl-pyrrol-2-yl      CH.sub.2 O                                      1227 N-methyl-pyrrol-3-yl      CH.sub.2 O                                      1228 N-methyl-pyrazol-3-yl     CH.sub.2 O                                      1229 N-methy-pyrazol-4-yl      CH.sub.2 O                                      1230 N-methyl-pyrazol-5-yl     CH.sub.2 O                                      1231 N-methyl-imidazol-2-yl    CH.sub.2 O                                      1232 N-methyl-imidazol-4-yl    CH.sub.2 O                                      1233 N-methyl-imidazol-5-yl    CH.sub.2 O                                      1234 1-methyl-1,2,3-triazol-4-yl                                                                              CH.sub.2 O                                      1235 1-methyl-1,2,3-triazol-5-yl                                                                              CH.sub.2 O                                      1236 1-methyl-1,2,4-triazol-3-yl                                                                              CH.sub.2 O                                      1237 1-methyl-1,2,4-triazol-5-yl                                                                              CH.sub.2 O                                      1238 1-methyl-tetrazol-5-yl    CH.sub.2 O                                      1239 isoxazol-3-yl             CH.sub.2 O                                      1240 isoxazol-4-yl             CH.sub.2 O                                      1241 isoxazol-5-yl             CH.sub.2 O                                      1242 benzisoxazol-3-yl         CH.sub.2 O                                      1243 benzoxazol-2-yl           CH.sub.2 O                                      1244 oxazol-2-yl               CH.sub.2 O                                      1245 oxazol-4-yl               CH.sub.2 O                                      1246 oxazol-5-yl               CH.sub.2 O                                      1247 thiazol-2-yl              CH.sub.2 O                                      1248 thiazol-4-yl              CH.sub.2 O                                      1249 thiazol-5-yl              CH.sub.2 O                                      1250 benzthiasol-2-yl          CH.sub.2 O                                      1251 benzisothiazol-3-yl       CH.sub.2 O                                      1252 isothiazol-3-yl           CH.sub.2 O                                      1253 isothiazol-4-yl           CH.sub.2 O                                      1254 isothiazol-5-yl           CH.sub.2 O                                      1255 1,2,3-thiadiazol-4-yl     CH.sub.2 O                                      1256 1,2,4-thiadiazol-5-yl     CH.sub.2 O                                      1257 1,3,4-thiadiazol-3-yl     CH.sub.2 O                                      1258 2-furyl                   O                                               1259 5-nitro-2-furyl           O                                               1260 5-chloro-2-furyl          O                                               1261 3-furyl                   O                                               1262 5-nitro-3-furyl           O                                               1263 5-chloro-3-furyl          O                                               1264 benzofuran-2-yl           O                                               1265 benzofuran-3-yl           O                                               1266 2-thienyl                 O                                               1267 5-nitro-2-thienyl         O                                               1268 5-chloro-2-thienyl        O                                               1269 3-thienyl                 O                                               1270 5-nitro-3-thienyl         O                                               1271 5-chloro-3-thienyl        O                                               1272 benzothien-2-yl           O                                               1273 benzothien-3-yl           O                                               1274 N-methyl-pyrrol-2-yl      O                                               1275 N-methyl-pyrrol-3-yl      O                                               1276 N-methyl-pyrazol-3-yl     O                                               1277 N-methyl-pyrazol-4-yl     O                                               1278 N-methyl-pyrazol-5-yl     O                                               1279 N-methyl-imidazol-2-yl    O                                               1280 N-methyl-imidazol-4-yl    O                                               1281 N-methyl-imidazol-5-yl    O                                               1282 1-methyl-1,2,3-triazol-4-yl                                                                              O                                               1283 1-methyl-1,2,3-triazol-5-yl                                                                              O                                               1284 1-methyl-1,2,4-triazol-3-yl                                                                              O                                               1285 1-methyl-1,2,4-triazol-5-yl                                                                              O                                               1286 1-methyl-tetrazol-5-yl    O                                               1287 isoxazol-3-yl             O                                               1288 isoxazol-4-yl             O                                               1289 isoxazol-5-yl             O                                               1290 benzisoxazol-3-yl         O                                               1291 benzoxazol-2-yl           O                                               1292 oxazol-2-yl               O                                               1293 oxazol-4-yl               O                                               1294 oxazol-5-yl               O                                               1295 thiazol-2-yl              O                                               1296 thiazol-4-yl              O                                               1297 thiazol-5-yl              O                                               1298 benzthiazol-2-yl          O                                               1299 benzisothiazol-3-yl       O                                               1300 isothiazol-3-yl           O                                               1301 isothiazol-4-yl           O                                               1302 isothiazol-5-yl           O                                               1303 1,3-thiazolo[4,5-b]pyridin-2-yl                                                                          O                                               1304 2-furyl                   S                                               1305 5-nitro-2-furyl           S                                               1306 5-chloro-2-furyl          S                                               1307 3-furyl                   S                                               1308 5-nitro-3-furyl           S                                               1309 5-chloro-3-furyl          S                                               1310 benzofuran-2-yl           S                                               1311 benzofuran-3-yl           S                                               1312 2-thienyl                 S                                               1313 5-nitro-2-thienyl         S                                               1314 5-chloro-2-thienyl        S                                               1315 3-thienyl                 S                                               1316 5-nitro-3-thienyl         S                                               1317 5-chloro-3-thienyl        S                                               1318 benzothien-2-yl           S                                               1319 benzothien-3-yl           S                                               1320 N-methyl-pyrrol-2-yl       S                                              1321 N-methyl-pyrrol-3-yl      S                                               1322 N-methyl-pyrazol-3-yl     S                                               1323 N-methyl-pyrazol-4-yl     S                                               1324 N-methyl-pyrazol-5-yl     S                                               1325 N-methyl-imidazol-2-yl    S                                               1326 N-methyl-imidazol-4-yl    S                                               1327 N-methyl-imidazol-5-yl    S                                               1328 1-methyl-1,2,3-triazol-4-yl                                                                              S                                               1329 1-methyl-1,2,3-triazol-5-yl                                                                              S                                               1330 1-methyl-1,2,4-triazol-3-yl                                                                              S                                               1331 1-methyl-1,2,4-triazol-5-yl                                                                              S                                               1332 1-methyl-tetrazol-5-yl    S                                               1333 isoxazol-3-yl             S                                               1334 isoxazol-4-yl             S                                               1335 isoxazol-5-yl             S                                               1336 benzisoxazol-3-yl         S                                               1337 benzoxazol-2-yl           S                                               1338 oxazol-2-yl               S                                               1339 oxazol-4-yl               S                                               1340 oxazol-5-yl               S                                               1341 thiazol-2-yl              S                                               1342 oxazol-4-yl               S                                               1343 oxazol-5-yl               S                                               1344 thiazol-2-yl              S                                               1345 thiazol-4-yl              S                                               1346 thiazol-5-yl              S                                               1347 benzthiazol-2-yl          S                                               1348 benzisothiazol-3-yl       S                                               1349 isothiazol-3-yl           S                                               1350 isothiazol-4-yl           S                                               1351 isothiazol-5-yl           S                                               1352 1,3,-thiazolo[4,5-b]pyridin-2-yl                                                                         S                                               1353 2-furyl                   OCH.sub.2                                       1354 5-nitro-2-furyl           OCH.sub.2                                       1355 5-chloro-2-furyl          OCH.sub.2                                       1356 3-Furyl                   OCH.sub.2                                       1357 5-nitro-3-furyl           OCH.sub.2                                       1358 5-chloro-3-furyl          OCH.sub.2                                       1359 benzofuran-2-yl           OCH.sub.2                                       1360 benzofuran-3-yl           OCH.sub.2                                       1361 2-thienyl                 OCH.sub.2                                       1362 5-nitro-2-thienyl         OCH.sub.2                                       1363 5-chloro-2-thienyl        OCH.sub.2                                       1364 3-thienyl                 OCH.sub.2                                       1365 5-nitro-3-thienyl         OCH.sub.2                                       1366 5-chloro-3-thienyl        OCH.sub.2                                       1367 benzothien-2-yl           OCH.sub.2                                       1368 benzothien-3-yl           OCH.sub.2                                       1369 N-methyl-pyrrol-2-yl      OCH.sub.2                                       1370 N-methyl-pyrrol-3-yl      OCH.sub.2                                       1371 N-methyl-pyrazol-3-yl     OCH.sub.2                                       1372 N-methyl-pyrazol-4-yl     OCH.sub.2                                       1373 N-methyl-pyrazol-5-yl     OCH.sub.2                                       1374 N-methyl-imidazol-2-yl    OCH.sub.2                                       1375 N-methyl-imidazol-4-yl    OCH.sub.2                                       1376 N-methyl-imidazol-5-yl    OCH.sub.2                                       1377 1-methyl-1,2,3-triazol-4-yl                                                                              OCH.sub.2                                       1378 1-methyl-1,2,3-triazol-5-yl                                                                              OCH.sub.2                                       1379 1-methyl-1,2,4-triazol-3-yl                                                                              OCH.sub.2                                       1380 1-methyl-1,2,4-triazol-5-yl                                                                              OCH.sub.2                                       1381 1-methyl-tetrazol-5-yl    OCH.sub.2                                       1382 isoxazol-3-yl             OCH.sub.2                                       1383 isoxazol-4-yl             OCH.sub.2                                       1384 isoxazol-5-yl             OCH.sub.2                                       1385 benzisoxazol-3-yl         OCH.sub.2                                       1386 benzoxazol-2-yl           OCH.sub.2                                       1387 oxazol-2-yl               OCH.sub.2                                       1389 oxazol-4-yl               OCH.sub.2                                       1390 oxazol-5-yl               OCH.sub.2                                       1391 thiazol-2-yl              OCH.sub.2                                       1392 thiazol-4-yl              OCH.sub.2                                       1393 thiazol-5-yl              OCH.sub.2                                       1394 benzthiazol-2-yl          OCH.sub.2                                       1395 benzisothiazol-3-yl       OCH.sub.2                                       1396 isothiazol-3-yl           OCH.sub.2                                       1397 isothiazol-4-yl           OCH.sub.2                                       1398 isothiazol-5-yl           OCH.sub.2                                       1399 2-furyl                   SCH.sub.2                                       1400 5-nitro-2-furyl           SCH.sub.2                                       1401 5-chloro-2-furyl          SCH.sub.2                                       1402 3-furyl                   SCH.sub.2                                       1403 5-nitro-3-furyl           SCH.sub.2                                       1404 5-chloro-3-furyl          SCH.sub.2                                       1405 benzofuran-2-yl           SCH.sub.2                                       1406 benzofuran-3-yl           SCH.sub.2                                       1407 2-thienyl                 SCH.sub.2                                       1408 5-nitro-2-thienyl         SCH.sub.2                                       1409 5-chloro-2-thienyl        SCH.sub.2                                       1410 3-thienyl                 SCH.sub.2                                       1411 5-nitro-3-thienyl         SCH.sub.2                                       1412 5-chloro-3-thienyl        SCH.sub.2                                       1413 benzothien-2-yl           SCH.sub.2                                       1414 benzothien-3-yl           SCH.sub.2                                       1415 N-methyl-pyrrol-2-yl      SCH.sub.2                                       1416 N-methyl-pyrrol-3-yl      SCH.sub.2                                       1417 N-methyl-pyrazol-3-yl     SCH.sub.2                                       1418 N-methyl-pyrazol-4-yl     SCH.sub.2                                       1419 N-methyl-pyrazol-5-yl     SCH.sub.2                                       1420 N-methyl-imidazol-2-yl    SCH.sub.2                                       1421 N-methyl-imidazol-4-yl    SCH.sub.2                                       1422 N-methyl-imidazol-5-yl    SCH.sub.2                                       1423 1-methyl-1,2,3-triazol-4-yl                                                                              SCH.sub.2                                       1424 1-methyl-1,2,3-triazol-5-yl                                                                              SCH.sub.2                                       1425 1-methyl-1,2,4-triazol-3-yl                                                                              SCH.sub.2                                       1426 1-methyl-1,2,4-triazol-5-yl                                                                              SCH.sub. 2                                      1427 1-methyl-tetrazol-5-yl    SCH.sub.2                                       1428 isoxazol-3-yl             SCH.sub.2                                       1429 isoxazol-4-yl             SCH.sub.2                                       1430 isoxazol-5-yl             SCH.sub.2                                       1431 benzisoxazol-3-yl         SCH.sub.2                                       1432 benzoxazol-2-yl           SCH.sub.2                                       1433 oxazol-2-yl               SCH.sub.2                                       1434 oxazol-4-yl               SCH.sub.2                                       1435 oxazol-5-yl               SCH.sub.2                                       1436 thiazol-2-yl              SCH.sub.2                                       1437 thiazol-4-yl              SCH.sub.2                                       1438 thiazol-5-yl              SCH.sub.2                                       1439 benzthiazol-2-yl          SCH.sub.2      oil; .sup.1 H-NMR                                                              (CDCl.sub.3):                                                                  δ = 3.78(3H),                                                            4.58(2H),                                                                      5.83(1H), 6.63(1H),                                                            7.1-7.9(8H)                      1440 benzisothiazol-3-yl       SCH.sub.2                                       1441 isothiazol-3-yl           SCH.sub.2                                       1442 isothiazol-4-yl           SCH.sub.2                                       1443 isothiazol-5-yl           SCH.sub.2                                       1444 1,2,3-thiadiazol-4-yl     SCH.sub.2                                       1445 1,2,4-thiadiazol-5-yl     SCH.sub.2                                       1446 1,3,4-thiadiazol-3-yl     SCH.sub.2                                       1447 2-furyl                   COOCH.sub.2                                     1448 5-nitro-2-furyl           COOCH.sub.2                                     1449 5-chloro-2-furyl          COOCH.sub.2                                     1450 2-(2'-furyl)-ethenyl      COOCH.sub.2                                     1451 2-(5'-nitro-2'furyl)ethenyl                                                                              COOCH.sub.2                                     1452 3-furyl                   COOCH.sub.2                                     1453 5-nitro-3-furyl           COOCH.sub.2                                     1454 5-chloro-3-furyl          COOCH.sub.2                                     1455 2-(3'-furyl)ethenyl       COOCH.sub.2                                     1456 2-(5'-nitro-3'-furanyl)ethenyl                                                                           COOCH.sub.2                                     1457 benzofuran-2-yl           COOCH.sub.2                                     1458 benzofuran-3-yl           COOCH.sub.2                                     1459 2-thienyl                 COOCH.sub.2                                     1460 5-nitro-2-thienyl         COOCH.sub.2                                     1461 5-chloro-2-thienyl        COOCH.sub.2                                     1462 2-(2'-thienyl)ethenyl     COOCH.sub.2                                     1463 2-(5'-nitro-2'-thienyl)ethenyl                                                                           COOCH.sub.2                                     1464 3-thienyl                 COOCH.sub.2                                     1465 5-nitro-3-thienyl         COOCH.sub.2                                     1466 5-chloro-3-thienyl        COOCH.sub.2                                     1467 2-(3'-thienyl)ethenyl     COOCH.sub.2                                     1468 2-(5'-nitro-3'-thienyl)ethenyl                                                                           COOCH.sub.2                                     1469 benzothien-2-yl           COOCH.sub.2                                     1470 benzothien-3-yl           COOCH.sub.2                                     1471 N-methyl-pyrrol-2-yl      COOCH.sub.2                                     1472 N-methyl-pyrrol-3-yl      COOCH.sub.2                                     1473 N-methyl-pyrazol-3-yl     COOCH.sub.2                                     1474 N-methyl-pyrazol-4-yl     COOCH.sub.2                                     1475 N-methyl-pyrazol-5-yl     COOCH.sub.2                                     1476 N-methyl-imidazol-2-yl    COOCH.sub.2                                     1477 N-methyl-imidazol-4-yl    COOCH.sub.2                                     1478 N-methyl-imidazol-5-yl    COOCH.sub.2                                     1479 1-methyl-1,2,3-triazol-4-yl                                                                              COOCH.sub.2                                     1480 1-methyl-1,2,3-triazol-5-yl                                                                              COOCH.sub.2                                     1481 1-methyl-1,2,4-triazol-3-yl                                                                              COOCH.sub.2                                     1482 1-methyl-1,2,4-triazol-5-yl                                                                              COOCH.sub.2                                     1483 1-methyl-tetrazol-5-yl    COOCH.sub.2                                     1484 isoxazol-3-yl             COOCH.sub.2                                     1485 isoxazol-4-yl             COOCH.sub.2                                     1486 isoxazol-5-yl             COOCH.sub.2                                     1487 benzisoxazol-3-yl         COOCH.sub.2                                     1488 benzoxazol-2-yl           COOCH.sub.2                                     1489 oxazol-2-yl               COOCH.sub.2                                     1490 oxazol-4-yl               COOCH.sub.2                                     1491 oxazol-5-yl               COOCH.sub.2                                     1492 thiazol-2-yl              COOCH.sub.2                                     1493 thiazol-4-yl              COOCH.sub.2                                     1494 thiazol-5-yl              COOCH.sub.2                                     1495 benzthiasol-2-yl          COOCH.sub.2                                     1496 benzisothiazol-3-yl       COOCH.sub.2                                     1497 isothiazol-3-yl           COOCH.sub.2                                     1498 isothioazol-4-yl          COOCH.sub.2                                     1499 isothiazol-5-yl           COOCH.sub.2                                     1500 1,2,3-thiadiazol-4-yl     COOCH.sub.2                                     1501 1,2,4-thiadiazol-5-yl     COOCH.sub.2                                     1502 1,3,4-thiadiazol-3-yl     COOCH.sub.2                                     1503 2-furyl                   NHCOO                                           1504 5-nitro-2-furyl           NHCOO                                           1505 5-chloro-2-furyl          NHCOO                                           1506 3-furyl                   NHCOO                                           1507 5-nitro-3-furyl           NHCOO                                           1508 5-chloro-3-furyl          NHCOO                                           1509 benzofuran-2-yl           NHCOO                                           1510 benzofuran-3-yl           NHCOO                                           1511 2-thienyl                 NHCOO                                           1512 5-nitro-2-thienyl         NHCOO                                           1513 5-chloro-2-thienyl        NHCOO                                           1514 3-thienyl                 NHCOO                                           1515 5-nitro-3-thienyl         NHCOO                                           1516 5-chloro-3-thienyl        NHCOO                                           1517 benzothien-2-yl           NHCOO                                           1518 benzothien-3-yl           NHCOO                                           1519 N-methyl-pyrrol-2-yl      NHCOO                                           1520 N-methyl-pyrrol-3-yl      NHCOO                                           1521 N-methyl-pyrazol-3-yl     NHCOO                                           1522 N-methyl-pyrazol-4-yl     NHCOO                                           1523 N-methyl-pyrazol-5-yl     NHCOO                                           1524 N-methyl-imidazol-4-yl    NHCOO                                           1526 N-methyl-imidazol-5-yl    NHCOO                                           1527 1-methyl-1,2,3-triazol-4-yl                                                                              NHCOO                                           1528 1-methyl-1,2,3-triazol-5-yl                                                                              NHCOO                                           1529 1-methyl-1,2,4-triazol-3-yl                                                                              NHCOO                                           1530 1-methyl-1,2,4-triazol-5-yl                                                                              NHCOO                                           1531 1-methyl-tetrazol-5-yl    NHCOO                                           1532 isoxazol-3-yl             NHCOO                                           1533 isoxazol-4-yl             NHCOO                                           1534 isoxazol-5-yl             NHCOO                                           1535 benzisoxazol-3-yl         NHCOO                                           1536 benzoxazol-2-yl           NHCOO                                           1537 oxazol-2-yl               NHCOO                                           1538 oxazol-4-yl               NHCOO                                           1539 oxazol-5-yl                NHCOO                                          1540 thiazol-2-yl              NHCOO                                           1541 thiazol-4-yl              NHCOO                                           1542 thiazol-5-yl              NHCOO                                           1543 benzthiazol-2-yl          NHCOO                                           1544 benzisothiazol-3-yl       NHCOO                                           1545 isothiazol-3-yl           NHCOO                                           1546 isothiazol-4-yl           NHCOO                                           1547 isothiazol-5-yl           NHCOO                                           1548 2-furyl                   COO                                             1549 5-nitro-2-furyl           COO                                             1550 5-chloro-2-furyl          COO                                             1551 2-(2'-furyl)-ethenyl      COO                                             1552 2-(5'-nitro-2'-furyl)ethenyl                                                                             COO                                             1553 3-furyl                   COO                                             1554 5-nitro-3-furyl           COO                                             1555 5-chloro-3-furyl          COO                                             1556 2-(3'-furyl)ethenyl       COO                                             1557 2-(5'-nitro-3'-furanyl)ethenyl                                                                           COO                                             1558 benzofuran-2-yl           COO                                             1559 benzofuran-3-yl           COO                                             1560 2-thienyl                 COO                                             1561 5-nitro-2-thienyl         COO                                             1562 5-chloro-2-thienyl        COO                                             1563 2-(2'-thienyl)ethenyl     COO                                             1564 2-(5'-nitro-2'-thienyl)ethenyl                                                                           COO                                             1565 3-thienyl                 COO                                             1566 5-nitro-3-thienyl         COO                                             1567 5-chloro-3-thienyl        COO                                             1568 2-(3'-thienyl)ethenyl     COO                                             1569 2-(5'-nitro-3'-thienyl)ethenyl                                                                           COO                                             1570 benzothien-2-yl           COO                                             1571 benzothien-3-yl           COO                                             1572 N-methyl-pyrrol-2-yl      COO                                             1573 N-methyl-pyrrol-3-yl      COO                                             1574 N-methyl-pyrazol-3-yl     COO                                             1575 N-methyl-pyrazol-4-yl     COO                                             1576 N-methyl-pyrazol-5-yl     COO                                             1577 N-methyl-imidazol-2-yl    COO                                             1578 N-methyl-imidazol-4-yl    COO                                             1579 N-methyl-imidazol-5-yl    COO                                             1580 1-methyl-1,2,3-triazol-4-yl                                                                              COO                                             1581 1-methyl-1,2,3-triazol-5-yl                                                                              COO                                             1582 1-methyl-1,2,4-triazol-3-yl                                                                              COO                                             1583 1-methyl-1,2,4-triazol-5-yl                                                                              COO                                             1584 1-methyl-tetrazol-5-yl    COO                                             1585 isoxazol-3-yl             COO                                             1586 isoxazol-4-yl             COO                                             1587 isoxazol-5-yl             COO                                             1588 benzisoxazol-3-yl         COO                                             1589 benzoxazol-2-yl           COO                                             1590 oxazol-2-yl               COO                                             1591 oxazol-4-yl               COO                                             1592 oxazol-5-yl               COO                                             1593 thiazol-2-yl              COO                                             1594 thiazol-4-yl              COO                                             1595 thiazol-5-yl              COO                                             1596 benzthiazol-2-yl          COO                                             1597 benzisothiazol-3-yl       COO                                             1598 isothiazol-3-yl           COO                                             1599 isothioazol-4-yl          COO                                             1600 isothiazol-5-yl           COO                                             1601 1,2,3-isodiazol-4-yl      COO                                             1602 1,2,4-thiadiazol-5-yl     CO O                                            1603 1,3,4-thiadiazol-3-yl     COO                                             1604 2-furyl                   OCO                                             1605 5-nitro-2-furyl           OCO                                             1606 5-chloro-2-furyl          OCO                                             1607 3-furyl                   OCO                                             1608 5-nitro-3-furyl           OCO                                             1609 5-chloro-3-furyl          OCO                                             1610 benzofuran-2-yl           OCO                                             1611 benzofuran-3-yl           OCO                                             1612 2-thienyl                 OCO                                             1613 5-nitro-2-thienyl         OCO                                             1614 5-chloro-2-thienyl        OCO                                             1615 3-thienyl                 OCO                                             1616 5-nitro-3-thienyl         OCO                                             1617 5-chloro-3-thienyl        OCO                                             1618 benzothien-2-yl           OCO                                             1619 benzothien-3-yl           OCO                                             1620 N-methyl-pyrrol-2-yl      OCO                                             1621 N-methyl-pyrrol-3-yl      OCO                                             1622 N-methyl-pyrazol-3-yl     OCO                                             1623 N-methyl-pyrazol-4-yl     OCO                                             1625 N-methyl-imidazol-2-yl    OCO                                             1626 N-methyl-imidazol-4-yl    OCO                                             1627 N-methyl-imidazol-5-yl    OCO                                             1628 1-methyl-1,2,3-triazol-4-yl                                                                              OCO                                             1629 1-methyl-1,2,3-triazol-5-yl                                                                              OCO                                             1630 1-methyl-1,2,4-triazol-3-yl                                                                              OCO                                             1631 1-methyl-1,2,4-triazol-5-yl                                                                              OCO                                             1632 1-methyl-tetrazol-5-yl    OCO                                             1633 isoxazol-3-yl             OCO                                             1634 isoxazol-4-yl             OCO                                             1635 isoxazol-5-yl             OCO                                             1636 benzoisoxazol-3-yl        OCO                                             1637 benzoxazol-2-yl           OCO                                             1638 oxazol-2-yl               OCO                                             1639 oxazol-4-yl               OCO                                             1640 oxazol-5-yl               OCO                                             1641 thiazol-2-yl              OCO                                             1642 thiazol-4-yl              OCO                                             1643 thiazol-5-yl              OCO                                             1644 benzthiazol-2-yl          OCO                                             1645 benzisothiazol-3-yl       OCO                                             1646 isothiazol-3-yl           OCO                                             1647 isothiazol-4-yl           OCO                                             1648 isothiazol-5-yl           OCO                                             1649 1,2,3-thiadiazol-4-yl     OCO                                             1650 1,2,4-thiadiazol-5-yl     OCO                                             1651 1,3,4-thiadiazol-3-yl     OCO                                             1652 6-chloro-benzothiazol-2-yl                                                                               SCH.sub.2      oil; .sup.1 H-NHR                                                              (CDCl.sub.3):                                                                  δ = 3.78(3H),                                                            4.53(2H),                                                                      5.84(1H), 6.62(1H),                                                            7.1-7.8(7H)                      __________________________________________________________________________

Generally speaking, the novel compounds are extremely effective on a broad spectrum of phytopathogenic fungi, in particular those from the Ascomycetes and Basidiomycetes classes. Some of them have a systemic action and can be used as foliar and soil fungicides.

The fungicidal compounds are of particular interest for controlling a large number of fungi in various crops or their seeds, especially wheat, rye, barley, oats, rice, Indian corn, lawns, cotton, soybeans, coffee, sugar cane, fruit and ornamentals in horticulture and viticulture, and in vegetables such as cucumbers, beans and cucurbits.

The novel compounds are particularly useful for controlling the following plant diseases:

Erysiphe graminis in cereals,

Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits,

Podosphaera leucotricha in apples,

Uncinula necator in vines,

Puccinia species in cereals,

Rhizoctonia species in cotton and lawns,

Ustilago species in cereals and sugar cane,

Venturia inaequalis (scab) in apples,

Helminthosporium species in cereals,

Septoria nodorum in wheat,

Botrytis cinerea (gray mold) in strawberries and grapes,

Cercospora arachidicola in groundnuts,

Pseudocercosporella herpotrichoides in wheat and barley,

Pyricularia oryzae in rice,

Phytophthora infestans in potatoes and tomatoes,

Fusarium and Verticillium species in various plants,

Plasmopara viticola in grapes,

Alternaria species in fruit and vegetables.

The compounds are applied by spraying or dusting the plants with the active ingredients, or treating the seeds of the plants with the active ingredients. They may be applied before or after infection of the plants or seeds by the fungi.

The novel substances can be converted into conventional formulations such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application forms depend entirely on the purposes for which they are intended; they should at all events ensure a fine and uniform distribution of the active ingredient. The formulations are produced in known manner, for example by extending the active ingredient with solvents and/or carriers, with or without the use of emulsifiers and dispersants; if water is used as solvent, it is also possible to employ other organic solvents as auxiliary solvents. Suitable auxiliaries for this purpose are solvents such as aromatics (e.g., xylene), chlorinated aromatics (e.g., chlorobenzenes), paraffins (e.g., crude oil fractions), alcohols (e.g., methanol, butanol), ketones (e.g., cyclohexanone), amines (e.g., ethanolamine, dimethylformamide), and water; carriers such as ground natural minerals (e.g., kaolins, aluminas, talc and chalk) and ground synthetic minerals (e.g., highly disperse silica and silicates); emulsifiers such as nonionic and anionic emulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates); and dispersants such as lignin, sulfite waste liquors and methylcellulose.

The fungicidal agents generally contain from 0.1 to 95, and preferably from 0.5 to 90wt % of active ingredient. The application rates are from 0.02 to 3 kg or more of active ingredient per hectare, depending on the type of effect desired. The novel compounds may also be used for protecting materials, for example against Paecilomyces variotii.

The agents and the ready-to-use formulations prepared from them, such as solutions, emulsions, suspensions, powders, dusts, pastes and granules, are applied in conventional manner, for example by spraying, atomizing, dusting, scattering, dressing or watering.

Examples of formulations are given below.

I. 90 parts by weight of compound no. 460 is mixed with 10 parts by weight of N-methyl-α-pyrrolidone. A mixture is obtained which is suitable for application in the form of very fine drops.

II. 20 parts by weight of compound no. 632 is dissolved in a mixture consisting of 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into water and uniformly distributing it therein, an aqueous dispersion is obtained.

III. 20 parts by weight of compound no. 649 is dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into water and finely distributing it therein, an aqueous dispersion is obtained.

IV. 20 parts by weight of compound no. 773 is dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210° and 280° C., and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into water and uniformly distributing it therein, an aqueous dispersion is obtained.

V. 80 parts by weight of compound no. 866 is well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 10 parts by weight of the sodium salt of a lignin-sulfonic acid obtained from a sulfite waste liquor, and 7 parts by weight of powdered silica gel, and triturated in a hammer mill. By uniformly distributing the mixture in water, a spray liquor is obtained.

VI. 3 parts by weight of compound no. 866 is intimately mixed with 97 parts by weight of particulate kaolin. A dust is obtained containing 3% by weight of the active ingredient.

VII 30 parts by weight of compound no. 460 is intimately mixed with a mixture consisting of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. A formulation of the active ingredient is obtained having good adherence.

VIII. 40 parts by weight of compound no. 632 is intimately mixed with 10 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts of water to give a stable aqueous dispersion. Dilution in water gives an aqueous dispersion.

IX. 20 parts by weight of compound no. 649 is intimately mixed with 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of a fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. A stable oily dispersion is obtained.

In these application forms, the agents according to the invention may also be present together with other active ingredients, for example herbicides, insecticides, growth regulators, and fungicides, and may furthermore be mixed and applied together with fertilizers. Admixture with other fungicides frequently results in an increase in the fungicidal spectrum.

The following list of fungicides with which the novel compounds may be combined is intended to illustrate possible combinations but not to impose any restrictions.

Examples of fungicides which may be combined with the novel compounds are:

sulfur,

dithiocarbamates and their derivatives, such as

ferric dimethyldithiocarbamate,

zinc dimethyldithiocarbamate,

zinc ethylenebisdithiocarbamate,

manganese ethylenebisdithiocarbamate,

manganese zinc ethylenediaminebisdithiocarbamate,

tetramethylthiuram disulfides,

ammonia complex of zinc N,N'-ethylenebisdithiocarbamate,

ammonia complex of zinc N,N'-propylenebisdithiocarbamate,

zinc N,N'-propylenebisdithiocarbamate and

N,N'-polypropylenebis(thiocarbamyl) disulfide;

nitro derivatives, such as

dinitro(1-methylheptyl)-phenyl crotonate,

2-sec-butyl-4,6-dinitrophenyl 3,3-dimethylacrylate,

2-sec-butyl-4,6-dinitrophenyl isopropylcarbonate and

diisopropyl 5-nitroisophthalate;

heterocyclic substances, such as

2-heptadecylimidazol-2-yl acetate,

2,4-dichloro-6-(o-chloroanilino)-s-triazine,

O,O-diethyl phthalimidophosphonothioate,

5-amino-1-[-bis-(dimethylamino)-phosphinyl]-3-phenyl-1,2,4-triazole,

2,3-dicyano-1,4-dithioanthraquinone,

2-thio-1,3-dithio[4,5-b]quinoxaline,

methyl 1-(butylcarbamyl)-2-benzimidazolecarbamate,

2-methoxycarbonylaminobenzimidazole,

2-(fur-2-yl)-benzimidazole,

2-(thiazol-4-yl)benzimidazole,

N-(1,1,2,2-tetrachloroethylthio)-tetrahydrophthalimide,

N-trichloromethylthiotetrahydrophthalimide,

N-trichloromethylthiophthalimide,

N-dichlorofluoromethylthio-N',N'-dimethyl-N-phenylsulfuric acid diamide,

5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole,

2-thiocyanatomethylthiobenzothiazole,

1,4-dichloro-2,5-dimethoxybenzene,

4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone,

2-thiopyridine 1-oxide,

8-hydroxyquinoline and its copper salt,

2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiyne,

2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiyne 4,4-dioxide,

2-methylfuran-3-carboxanilide,

3 2,5-dimethylfuran-3-carboxanilide,

2,4,5-trimethylfuran-3-carboxanilide,

2,5-dimethyl-N-cyclohexylfuran-3-carboxamide,

N-cyclohexyl-N-methoxy-2,5-diethylfuran-3-carboximide,

2-methylbenzanilide,

2-iodobenzanilide,

N-formyl-N-morpholine-2,2,2-trichloroethylacetal,

piperazine-1,4-diylbis-(1-(2,2,2-trichloroethyl)-formamide),

1-(3,4-dichloroanilino)-1-formylamino-2,2,2-trichloroethane,

2,6-dimethyl-N-tridecylmorpholine and its salts,

2,6-dimethyl-N-cyclododecylmorpholine and its salts,

N-[3-(p-tert.-butylphenyl)-2-methylpropyl]-cis-2,6-dimethylmorpholine,

N-[3-(p-tert.-butylphenyl)-2-methylpropyl]-piperidine,

1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole

1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole,

N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N'-imidazolyl-urea,

1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-butan-2-one,

1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-butan-2-ol,

1-(4-phenylphenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol,

α-(2-chlorophenyl)-α-(4-chlorophenyl)-5-pyrimidinemethanol,

5-butyl-(2-dimethylamino-4-hydroxy-6-methylpyrimidine,

bis-(p-chlorophenyl)-3-pyridinemethanol,

1,2-bis-(3-ethoxycarbonyl-2-thioureido)-benzene,

1,2-bis-(3-methoxycarbonyl-2-thioureido)-benzene,

and various fungicides, such as

dodecylguanidine acetate,

3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]-glutaramide, hexachlorobenzene,

DL-methyl-N-(2,6-dimethylphenyl)-N-fur-2-yl alanate,

methyl DL-N-(2,6-dimethylphenyl)-N-(2'-methoxyacetyl)-alanate,

N-(2,6-dimethylphenyl)-N-chloroacetyl-DL-2-aminobutyrolactone,

methyl DL-N-(2,6-dimethylphenyl)-N-(phenylacetyl)-alanate,

5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine,

3-[3,5-dichlorophenyl]-5-methyl-5-methoxymethyl-1,3-oxazolidine-2,4-dione,

3-(3,5-dichlorophenyl)-1-isopropylcarbamylhydantoin,

N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide,

2-cyano-[N-(ethylaminocarbonyl)-2-methoximino]-acetamide,

1-[2-(2,4-dichlorophenyl)-pentyl]-1H-1,2,4-triazole,

2,4-difluoro-α-(1H-1,2,4-triazol-1-ylmethyl)-benzhydryl alcohol,

N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-3-chloro-2-aminopyridine, and

1-((bis-(4-fluorophenyl)-methylsilyl)-methyl)-1H-1,2,4-triazole.

USE EXAMPLES

As comparative active ingredient, methyl α-phenylacrylate (A) disclosed in C.A. Reg. No. 1865-29-8 was used.

USE EXAMPLE 1 Action on Pyricularia oryzae (Protective)

Leaves of pot-grown rice seedlings of the "Bahia" variety were sprayed to runoff with aqueous emulsions consisting (dry basis) of 80% of active ingredient and 20% of emulsifier, and inoculated 24 hours later with an aqueous spore suspension of Pyricularia oryzae. The plants were then set up in climatic cabinets at 22° to 24° C. and a relative humidity of 95 to 99%. The extent of fungus spread was determined after 6 days.

The results show that active ingredients 460, 632, 649, 773 and 866, applied as 0.05 wt % spray liquors, had a better fungicidal action (95%) than prior art active ingredient A (60%).

USE EXAMPLE 2 Action on Pyrenophora teres

Barley seedlings of the "Igri" variety were sprayed to runoff at the two-leaf stage with aqueous suspensions consisting (dry basis) of 80% of active ingredient and 20% of emulsifier. After 24 hours the plants were inoculated with a spore suspension of the fungus Pyrenophora teres, and set up for 48 hours in a high-humidity climatic cabinet at 18° C. The plants were then cultivated for a further 5 days in the greenhouse at 20° to 22° C. and a relative humidity of 70° C. The extent of fungus spread was then assessed.

The results show that active ingredients 649 and 1439, applied as 0.05% spray liquors, had a better fungicidal action (90%) than prior art comparative compound A (0%).

USE EXAMPLE 3 Action on Wheat Mildew

Leaves of pot-grown wheat seedlings of the "Kanzler" variety were sprayed to runoff with aqueous liquors consisting (dry basis) of 80% of active ingredient and 20% of emulsifier, and dusted, 24 hours after the sprayed-on layer had dried, with spores or wheat mildew (Erisyphe graminis var. tritici). The plants were set up in the greenhouse at from 20° to 22° C. and a relative humidity of from 75 to 80%. The extent of mildew spread was determined after 7 days.

The results show that active ingredients 632 and 649, applied as 0.025% spray liquors, had a better fungicidal action (90%) than prior art comparative agent A (40%). 

We claim:
 1. α-Arylacrylates of the formula I ##STR8## where Y is substituted or unsubstituted C₁ -C₄ -alkylene, substituted or unsubstituted C₂ -C₄ -alkenylene, C₂ -C₄ -alkynylene, or C₁ -C₁₀ -alkyleneoxy, andZ is hydrogen, halogen, C₁ -C₁₈ -alkyl, C₂ -C₁₈ -alkenyl, C₃ -C₁₈ -cycloalkyl, C₂ -C₄ -alkynyl, aryl, aryl-C₁ -C₁₀ -alkyl, aryl-C₂ -C₁₀ -alkenyl, aryloxy, aryloxy-C₁ -C₁₀ -alkyl, C₁ -C₄ -alkoxy-C₁ -C₁₀ -alkyl, halo-C₁ -C₁₀ -alkyl, or aryloxy-C₁ -C₄ -alkoxy, which are unsubstituted or substituted by halogen, C₁ -C₄ -alkyl, C₂ -C₄ -alkenyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, C₂ -C₄ -haloalkenyl, unsubstituted or substituted phenyl or unsubstituted or substituted phenoxy, with the proviso that Z-Y- is not CH₃ O--.
 2. A process for combating fungi, wherein the fungi, or the materials, plants, seed or the soil threatened by fungus attack are treated with a fungicidally effective amount of a compound of the formula I ##STR9## where Y is substituted or unsubstituted C₁ -Ch₄ -alkylene, substituted or unsubstituted C₂ -C₄ -alkenylene, C₂ -C₄ -alkynylene, or C₁ -C₁₀ -alkyleneoxy, andZ is hydrogen, halogen, C₁ -C₁₈ -alkyl, C₂ -C₁₈ -alkenyl, C₃ -C₈ -cycloalkyl, C₂ -C₄ -alkynyl, aryl, aryl-C₁ -C₁₀ -alkyl, aryl-C₂ -C₁₀ -alkenyl, aryloxy, aryloxy-C₁ -C₁₀ -alkyl, C₁ -C₄ -alkoxy-C₁ -C₁₀ -alkyl, halo-C₁ -C₁₀ -alkyl, or aryloxy-C₁ -C₄ -alkoxy, which are unsubstituted or substituted by halogen, C₁ -C₄ -alkyl, C₂ -C₄ -alkenyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, C₂ -C₄ -haloalkenyl, unsubstituted or substituted phenyl or unsubstituted or substituted phenoxy, with the proviso that Z-Y- is not CH₃ O--.
 3. A fungicide containing an inert carrier and a fungicidally effective amount of a compound of the formula I ##STR10## where Y is substituted or unsubstituted C₁ -C₄ -alkylene, substituted or unsubstituted C₂ -C₄ -alkenylene, C₂ -C₄ -alkynylene, or C₁ -C₁₀ -alkyleneoxy, andZ is hydrogen, halogen, C₁ -C₁₈ -alkyl, C₂ -C₁₈ -alkenyl, C₃ -C₈ -cycloalkyl, C₂ -C₄ -alkynyl, aryl, aryl-C₁ -C₁₀ -alkyl, aryl-C₂ -C₁₀ -alkenyl, aryloxy, aryloxy-C₁ -C₁₀ -alkyl, C₁ -C₄ -alkoxy-C₁ -C₁₀ -alkyl, halo-C₁ -C₁₀ -alkyl, or aryloxy-C₁ -C₄ -alkoxy, which are unsubstituted or substituted by halogen, C₁ -C₄ -alkyl, C₂ -C₄ -alkenyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, C₂ -C₄ -haloalkenyl, unsubstituted or substituted phenyl or unsubstituted or substituted phenoxy, with the proviso that Z-Y- is not CH₃ O--. 